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Hunan Wistar Imp. & Exp. Co., Ltd.

The company serves as a key global supplier of statins intermediates, which has a solid industrial foundation in the field of statins for lipid-lowering drugs, and holds a leading position in the market. Leveraging extensive experience in research an

High quality/Best price/Key global supplier/In stock/Express shipment/ ZT-5/CAS No.189028-95-3

Cas:189028-95-3

Min.Order:25 Kilogram

Negotiable

Type:Trading Company

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ACHIEVER SYSTEAM BIOCHEM CO., LTD.

We are specialized in custom synthesis, chemical/pharmaceutical/ pesticides outsourcing and contract research. We are committed to provide excellence in researching, manufacturing and drug discovery process. Our research team of scientists co

2-Oxazolidinone, 3-[(5S)-5-(4-fluorophenyl)-5-hydroxy-1-oxopentyl]-4-phenyl-, (4S)-

Cas:189028-95-3

Min.Order:0 Metric Ton

FOB Price: $1.0

Type:Lab/Research institutions

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Dayang Chem (Hangzhou) Co.,Ltd.

Dayangchem's R&D center can offer custom synthesis according to the contract research and development services for the fine chemicals, pharmaceutical, biotechnique and some of the other chemicals. DayangChem can provide different quantities

Simagchem Corporation

Welcome to Simagchem, your partner in China as a premier supply of bulk specialty chemicals for industry and life science. We introduce experienced quality product and exceptional JIT service with instant market intelligence in China to benefit our

Jinan Finer Chemical Co., Ltd

Product informations Product Name (S)-3-((S)-5-(4-Fluorophenyl)-5-hydroxypentanoyl)-4-phenyloxazolidin-2-one CAS No.

(S)-3-((S)-5-(4-Fluorophenyl)-5-hydroxypentanoyl)-4-phenyloxazolidin-2-one

Cas:189028-95-3

Min.Order:1 Gram

FOB Price: $8.0

Type:Lab/Research institutions

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Hangzhou Think Chemical Co. Ltd

Ezetimibe Intermediates 3-[(2R,5S)-5-(4-Fluorophenyl)-2-[(S)-[(4-fluorophenyl(amino)]][4-[trimethylsilyl]-oxy]phenyl]methyl]-1-oxo-5-[(trimethylsily)-oxy]pentyl]-4-phenyl-(4S)-2-oxazolidinone CAS:272778-12-8 N,O-Bis(trimethylsilyl)acetamide[CAS:104

(4S)-3-[(5S)-5-(4-Fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidin-2-one

Cas:189028-95-3

Min.Order:1 Kilogram

Negotiable

Type:Other

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Ality Chemical Corporation

The above product is Ality Chemical's strong item with best price, good quality and fast supply. Ality Chemical has been focusing on the research and production of this field for over 14 years. At the same time, we are always committed to providi

Henan Allgreen Chemical Co.,Ltd

Good quality Good price Promptly delivery Appearance:white powder Storage:dry dondition Application:intermediate Port:shanghai

189028-95-3 (4S)-3-[(5R)-5-(4-FLUOROPHENYL)-5-HYDROXYPENTANOYL]-4-PHENYL-1,3-OXAZOLIDIN-2-ONE

Cas:189028-95-3

Min.Order:1 Kilogram

Negotiable

Type:Manufacturers

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Xi'an Xszo Chem Co., Ltd.

1. Factory price and high quality must be guaranteed, base on 8 years of production and R&D experience2. Free samples will be provided,ensure specifications and quality are right for customer3. Customers will receive the most professional technical s

Chemwill Asia Co., Ltd.

Our main production base is located in Xuzhou industry park. We are certified both to the ISO 9001 and ISO 14001 Standards, have a safety management system in place.Our R&D team masters core technology for process-design of target building block

(S)-3-[(S)-5-(4-Fluorophenyl)-5-hydroxypentanoyl]-4-phenyloxazolidin-2-one

Cas:189028-95-3

Min.Order:5 Kiloliter

FOB Price: $1.2 / 5.0

Type:Manufacturers

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Henan Tianfu Chemical Co., Ltd.

TIANFUCHEM--189028-95-3-- (4S)-3-[(5R)-5-(4-FLUOROPHENYL)-5-HYDROXYPENTANOYL]-4-PHENYL-1,3-OXAZOLIDIN-2-ONE in stock Our company was built in 2009 with an ISO certificate.In the past 10 years, we have grown up as a famous fine chemicals supp

TIANFUCHEM--189028-95-3-- (4S)-3-[(5R)-5-(4-FLUOROPHENYL)-5-HYDROXYPENTANOYL]-4-PHENYL-1,3-OXAZOLIDIN-2-ONE in stock

Cas:189028-95-3

Min.Order:1 Metric Ton

FOB Price: $2000.0

Type:Lab/Research institutions

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LIDE PHARMACEUTICALS LIMITED

Advantage : LIDE PHARMACEUTICALS LIMITED is a professional chemicals and APIs leading manufacturer in China. Our core business line covers APIs, Intermediates, Herb extract, etc. We are specialized in chemical synthesis, process development of

(4S)-3-[(5R)-5-(4-FLUOROPHENYL)-5-HYDROXYPENTANOYL]-4-PHENYL-1,3-OXAZOLIDIN-2-ONE Manufacturer

Cas:189028-95-3

Min.Order:1 Kilogram

FOB Price: $1.0

Type:Lab/Research institutions

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Hebei Nengqian Chemical Import and Export Co., LTD

Our Advantage Rich Experience Our products are sold all over Europe,North&South America, Sino-East, Asia and pacific area as well as Africa,we establish long term. Quality service Company cooperates with research institutes. We strictly con

Top Quality CAS 189028-95-3 Ezetimibe Intermediate-6 Intermediate-6 Powder in Stock

Cas:189028-95-3

Min.Order:1 Kilogram

FOB Price: $1.0 / 10.0

Type:Trading Company

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Zhuozhou Wenxi import and Export Co., Ltd

WITH US,YOUR MONEY IN SAFE,YOUR BUSINESS IN SAFE 1)Quick Response Within 12 hours; 2)Quality Guarantee: All products are strictly tested by our QC, confirmed by QA and approved by third party lab in China, USA, Canada, Germany, UK, Italy, France et

Pharmaceutical Grade CAS 189028-95-3 with competitive price

Cas:189028-95-3

Min.Order:1 Kilogram

FOB Price: $139.0 / 210.0

Type:Trading Company

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Henan Sinotech Import&Export Corporation

Product Name: (4S)-3-[(5R)-5-(4-FLUOROPHENYL)-5-HYDROXYPENTANOYL]-4-PHENYL-1,3-OXAZOLIDIN-2-ONE Synonyms: (4S)-3-[(5R)-5-(4-FLUOROPHENYL)-5-HYDROXYPENTANOYL]-4-PHENYL-1,3-OXAZOLIDIN-2-ONE;(4S)-3-[(5S)-5-(4-

3-[(5S)-5-(4-fluorophenyl)-5-hydroxy-1-oxopentyl]-4-phenyl-, (4S)- 2-Oxazolidinone

Cas:189028-95-3

Min.Order:5 Metric Ton

FOB Price: $1.0 / 2.0

Type:Other

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Hubei Langyou International Trading Co., Ltd

1. Guaranteed purity; 2. Large quantity in stock; 3. Largest manufacturer; 4. Best service after shipment with email; 5. High quality & competitive price; Appearance:White Crystalline Powder Storage:Store in sealed conta

high quality 189028-95-3 Ezetimibe-003 with best price

Cas:189028-95-3

Min.Order:10 Gram

Negotiable

Type:Other

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HANWAYS CHEMPHARM CO.,LIMITED

Hanways chempharm is a specialized company concentrating on the R&D, production, marketing and technical service of APIs and pharmaceutical intermediates. The marketing department is located in Wuhan. We have two GMP facilities in Hubei Pr

High Purity Ezetimibe Intermediate CAS 189028-95-3

Cas:189028-95-3

Min.Order:1 Kilogram

FOB Price: $260.0 / 300.0

Type:Trading Company

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Shanghai Upbio Tech Co.,Ltd

1.No Less 8 years exporting experience. Clients can 100% received goods 2.Lower Price with higher quality 3,Free sample 4,We are sincerely responsible for the "product quality" and "After Service" Upbio is Specialized

(4S)-3-[(5S)-5-(4-Fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidin-2-one 189028-95-3

Cas:189028-95-3

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

Hangzhou Huarong Pharm Co., Ltd.

Hangzhou Huarong Pharm Co., Ltd. established since 2009 , has been always focusing on supplying products and services to our clients in the field of small molecule drug. Huarong Pharm has built platforms for the research, development and manufac

(4S)-3-[(5S)-5-(4-Fluoro phenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidin-2-one

Cas:189028-95-3

Min.Order:1 Gram

FOB Price: $1.0 / 2.0

Type:Lab/Research institutions

inquiry

Baoji Guokang Healthchem co.,ltd

Our company has been in existence for 10 years since its establishment. We have our own unique team. The company integrates independent research and development, production and sales. We have established famous brands at home and abroad. At prese

Qingdao Beluga Import and Export Co., LTD

(4S)-3-[(5R)-5-(4-FLUOROPHENYL)-5-HYDROXYPENTANOYL]-4-PHENYL-1,3-OXAZOLIDIN-2-ONE CAS: 189028-95-3 Qingdao Belugas Import and Export Co., Ltd. is a scientific and technological company integrating research and development, production and trade of ch

(4S)-3-[(5R)-5-(4-FLUOROPHENYL)-5-HYDROXYPENTANOYL]-4-PHENYL-1,3-OXAZOLIDIN-2-ONE CAS: 189028-95-3

Cas:189028-95-3

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Shandong Hanjiang Chemical Co., Ltd.

Hello, dear friend! I'm Hansen and Allen from China. Welcome to my lookchem mall! The following is a brief introduction of our company's products and services. If you are interested in our products, please contact us by emai

(4S)-3-[(5S)-5-(4-Fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidin-2-one

Cas:189028-95-3

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

Hebei Mojin Biotechnology Co.,Ltd

Hebei Mojin Biotechnology Co., Ltd, Our company is a professional chemical raw materials and chemical reagents research and development production enterprises. We have several production line,So we can control the lowest price. We also have several

cas:189028-95-3

Cas:189028-95-3

Min.Order:25 Gram

FOB Price: $90.0 / 100.0

Type:Trading Company

inquiry

Lonwin Chemical Group Limited

(4S)-3-[(5S)-5-(4-Fluorophenyl)-5-Hydroxypentanoyl]-4-Phenyl-1,3-Oxazolidin-2-One CAS: 189028-95-3 Specification Product Name (S)-3-((S)-5-(4-Fluorophenyl)-5-hydroxypentanoyl)-4-phenyloxazolidin-2-one CA

Henan Wentao Chemical Product Co., Ltd.

Henan Wentao Chemical Product Co.,Ltd is Located in Zhengzhou High-tech Development Zone with import and export license, We passed ISO 9001:2008 as well, Henan Wentao has developed more than 1000 compounds, which are widely used in the fields of prod

(4S)-3-[(5S)-5-(4-Fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidin-2-one

Cas:189028-95-3

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

Xiamen Hisunny Chemical Co.,Ltd

Best quality & Attractive price & Professional service; Trial & Pilot & Commercial Hisunny Chemical is a leading manufacturer and supplier of chemicals in China. We develop produce and distribute high quality intermediates, specia

(4S)-3-[(5S)-5-(4-Fluorophenyl)-5-Hydroxypentanoyl]-4-Phenyl-1,3-Oxazolidin-2-One

Cas:189028-95-3

Min.Order:0

Negotiable

Type:Manufacturers

inquiry

Afine Chemicals Limited

Our Services 1. New Molecules R&D 2. Own test center HPLC NMR GC LC-MS 3. API and Intermediates from China reputed manufacturers 4. Documents support COA MOA MSDS DMF open part Our advantages 1. Government awarded company. Top 100 enter

(4S)-3-[(5S)-5-(4-Fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidin-2-one

Cas:189028-95-3

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

Hangzhou Keyingchem Co.,Ltd

Hangzhou KeyingChem Co., Ltd. exported this product to many countries and regions at best price. If you are looking for the material’s manufacturer or supplier in China, KeyingChem is your best choice. Pls contact with us freely for getting det

(4S)-3-[(5R)-5-(4-FLUOROPHENYL)-5-HYDROXYPENTANOYL]-4-PHENYL-1,3-OXAZOLIDIN-2-ONE

Cas:189028-95-3

Min.Order:0 Metric Ton

Negotiable

Type:Lab/Research institutions

inquiry

SHANGHAI T&W PHARMACEUTICAL CO., LTD.

A substitute for perfluorooctanoic acid, mainly used as a surfactant, dispersant, additive, etc Appearance:White solid or Colorless liquid Purity:99.3 % We will ship the goods in a timely manner as required We can provide relevant documents acc

Shanghai Hope Chem Co., Ltd

1. Product advantages: exquisite appearance and unique functions. 2. Product Advantages: Our products are the best,fast speed ,in large stock 3. High-quality products and thoughtful service are your greatest satisfaction. 4. The product

(4S)-3-[(5S)-5-(4-Fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidin-2-one

Cas:189028-95-3

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

Synthetic route

(S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione
189028-93-1

(S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one
189028-95-3

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

Conditions
ConditionsYield
Stage #1: (S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione With TarB-N02 In tetrahydrofuran at 20℃; for 0.5h;
Stage #2: With lithium borohydride In tetrahydrofuran for 0.666667h; Reagent/catalyst; enantioselective reaction;
96%
Stage #1: (S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione With dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole In dichloromethane; toluene at -5 - 0℃; for 4 - 6h;
Stage #2: With sulfuric acid; dihydrogen peroxide In methanol; dichloromethane; water; toluene for 0.25h;
95%
Stage #1: With dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole In dichloromethane; toluene at -5 - 0℃; for 0.25h;
Stage #2: (S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione In dichloromethane; toluene at -5 - 0℃; for 4 - 6h;
95%
vinyl acetate
108-05-4

vinyl acetate

(R,S)-3-[5-(4-fluorophenyl)-5-hydroxy-pentanoyl]-4-phenyl-oxazolidin-2-one
1246853-48-4

(R,S)-3-[5-(4-fluorophenyl)-5-hydroxy-pentanoyl]-4-phenyl-oxazolidin-2-one

A

(R)-1-(4-fluorophenyl)-5-oxo-5-[(S)-2-oxo-4-phenyloxazolidin-3-yl]pentyl acetate
1246853-49-5

(R)-1-(4-fluorophenyl)-5-oxo-5-[(S)-2-oxo-4-phenyloxazolidin-3-yl]pentyl acetate

B

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one
189028-95-3

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

Conditions
ConditionsYield
Lipozyme TL IM In toluene at 20 - 40℃; Product distribution / selectivity;A 68%
B 74%
With Candida rugosa lipase In di-isopropyl ether at 35℃; for 120h; Solvent; Reagent/catalyst; Concentration; Enzymatic reaction;A n/a
B n/a
(S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione
189028-93-1

(S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione

A

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one
189028-95-3

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

B

(4S)-3-[(5R)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidin-2-one

(4S)-3-[(5R)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidin-2-one

C

(S)-3-[(S)-5-(4-Fluoro-phenyl)-1,5-dihydroxy-pentyl]-4-phenyl-oxazolidin-2-one

(S)-3-[(S)-5-(4-Fluoro-phenyl)-1,5-dihydroxy-pentyl]-4-phenyl-oxazolidin-2-one

Conditions
ConditionsYield
With borane-THF; boron trifluoride diethyl etherate; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole In tetrahydrofuran at 25℃; Product distribution; Further Variations:; Catalysts; Temperatures; acid additives, water content;
With BH3-DEA; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole In tetrahydrofuran; 1,2-dimethoxyethane; toluene at 40℃;
(S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione
189028-93-1

(S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione

A

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one
189028-95-3

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

B

(S)-3-[(S)-5-(4-Fluoro-phenyl)-1,5-dihydroxy-pentyl]-4-phenyl-oxazolidin-2-one

(S)-3-[(S)-5-(4-Fluoro-phenyl)-1,5-dihydroxy-pentyl]-4-phenyl-oxazolidin-2-one

Conditions
ConditionsYield
With sodium tetrahydroborate; dimethyl sulfate; N,N-diethylaniline; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole In tetrahydrofuran; toluene at 20℃; Product distribution; Further Variations:; Reagents; Temperatures;A 13 g
B n/a
(S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione
189028-93-1

(S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione

A

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one
189028-95-3

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

B

(4S)-3-[(5R)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidin-2-one

(4S)-3-[(5R)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidin-2-one

Conditions
ConditionsYield
Stage #1: (S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione With borane N,N-diethylaniline complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole In tetrahydrofuran; toluene at 18 - 20℃; for 1h;
Stage #2: With water; potassium carbonate In tetrahydrofuran; toluene at 20 - 30℃; for 0.5h;
Stage #1: (S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione With sodium tetrahydroborate; chloro-trimethyl-silane; (R)-α,α-diphenylprolinol In tetrahydrofuran at 24℃; for 3h; Heating / reflux;
Stage #2: With hydrogenchloride; water In tetrahydrofuran; toluene at 4℃; for 0.5h; Product distribution / selectivity;
A n/a
B n/a
Stage #1: (S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione With sodium tetrahydroborate; chloro-trimethyl-silane; (R)-2-[bis(4-trifluorophenyl)hydroxymethyl]pyrrolidine In tetrahydrofuran at 24℃; for 3h; Heating / reflux;
Stage #2: With hydrogenchloride; water In tetrahydrofuran; toluene at 4℃; for 0.5h; Product distribution / selectivity;
A n/a
B n/a
With chloro[(1S,2S)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine]-(mesitylene) ruthenium (II); formic acid/triethylamine complex 5:2 In tert-butyl methyl ether at 42℃; Reagent/catalyst; Solvent; Temperature; Inert atmosphere; stereoselective reaction;A n/a
B n/a
isopropyl alcohol
67-63-0

isopropyl alcohol

(S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione
189028-93-1

(S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one
189028-95-3

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

Conditions
ConditionsYield
With magnesium sulfate In triethanolamine(chloride)
C24H26FNO5

C24H26FNO5

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one
189028-95-3

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Candida rugosa lipase / di-isopropyl ether; aq. phosphate buffer / 120 h / 40 °C / Enzymatic reaction
2: Candida antarctica B lipase / toluene / 120 h / 35 °C / Enzymatic reaction
View Scheme
Multi-step reaction with 2 steps
1: Candida rugosa lipase / di-isopropyl ether; aq. phosphate buffer / 120 h / 40 °C / Enzymatic reaction
2: Candida antarctica B lipase / toluene / 120 h / 35 °C / Enzymatic reaction
View Scheme
C24H26FNO5

C24H26FNO5

A

(R)-1-(4-fluorophenyl)-5-oxo-5-[(S)-2-oxo-4-phenyloxazolidin-3-yl]pentyl acetate
1246853-49-5

(R)-1-(4-fluorophenyl)-5-oxo-5-[(S)-2-oxo-4-phenyloxazolidin-3-yl]pentyl acetate

B

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one
189028-95-3

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Candida rugosa lipase / di-isopropyl ether; aq. phosphate buffer / 120 h / 40 °C / Enzymatic reaction
2: Candida rugosa lipase / di-isopropyl ether / 120 h / 35 °C / Enzymatic reaction
View Scheme
Multi-step reaction with 3 steps
1: Candida rugosa lipase / di-isopropyl ether; aq. phosphate buffer / 120 h / 40 °C / Enzymatic reaction
2: triethylamine; dmap / dichloromethane / 4 h / 0 °C
3: Candida rugosa lipase / di-isopropyl ether; aq. phosphate buffer / 120 h / 40 °C / pH 6.2 / Enzymatic reaction
View Scheme
C24H26FNO5

C24H26FNO5

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one
189028-95-3

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Candida rugosa lipase / di-isopropyl ether; aq. phosphate buffer / 120 h / 40 °C / Enzymatic reaction
2: Candida antarctica B lipase / toluene / 120 h / 35 °C / Enzymatic reaction
View Scheme
Multi-step reaction with 2 steps
1: Candida rugosa lipase / di-isopropyl ether; aq. phosphate buffer / 120 h / 40 °C / Enzymatic reaction
2: Candida antarctica B lipase / toluene / 120 h / 35 °C / Enzymatic reaction
View Scheme
C24H26FNO5

C24H26FNO5

A

(R)-1-(4-fluorophenyl)-5-oxo-5-[(S)-2-oxo-4-phenyloxazolidin-3-yl]pentyl acetate
1246853-49-5

(R)-1-(4-fluorophenyl)-5-oxo-5-[(S)-2-oxo-4-phenyloxazolidin-3-yl]pentyl acetate

B

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one
189028-95-3

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Candida rugosa lipase / di-isopropyl ether; aq. phosphate buffer / 120 h / 40 °C / Enzymatic reaction
2: Candida rugosa lipase / di-isopropyl ether / 120 h / 35 °C / Enzymatic reaction
View Scheme
Multi-step reaction with 3 steps
1: Candida rugosa lipase / di-isopropyl ether; aq. phosphate buffer / 120 h / 40 °C / Enzymatic reaction
2: triethylamine; dmap / dichloromethane / 4 h / 0 °C
3: Candida rugosa lipase / di-isopropyl ether; aq. phosphate buffer / 120 h / 40 °C / pH 6.2 / Enzymatic reaction
View Scheme
(R,S)-3-[5-(4-fluorophenyl)-5-hydroxy-pentanoyl]-4-phenyl-oxazolidin-2-one
1246853-48-4

(R,S)-3-[5-(4-fluorophenyl)-5-hydroxy-pentanoyl]-4-phenyl-oxazolidin-2-one

A

(R)-1-(4-fluorophenyl)-5-oxo-5-[(S)-2-oxo-4-phenyloxazolidin-3-yl]pentyl acetate
1246853-49-5

(R)-1-(4-fluorophenyl)-5-oxo-5-[(S)-2-oxo-4-phenyloxazolidin-3-yl]pentyl acetate

B

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one
189028-95-3

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine; dmap / dichloromethane / 4 h / 0 °C
2: Candida rugosa lipase / di-isopropyl ether; aq. phosphate buffer / 120 h / 40 °C / pH 6.2 / Enzymatic reaction
View Scheme
Benzyl acetate
140-11-4

Benzyl acetate

(R,S)-3-[5-(4-fluorophenyl)-5-hydroxy-pentanoyl]-4-phenyl-oxazolidin-2-one
1246853-48-4

(R,S)-3-[5-(4-fluorophenyl)-5-hydroxy-pentanoyl]-4-phenyl-oxazolidin-2-one

A

(R)-1-(4-fluorophenyl)-5-oxo-5-[(S)-2-oxo-4-phenyloxazolidin-3-yl]pentyl acetate
1246853-49-5

(R)-1-(4-fluorophenyl)-5-oxo-5-[(S)-2-oxo-4-phenyloxazolidin-3-yl]pentyl acetate

B

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one
189028-95-3

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

C

(4S)-3-[(5R)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidin-2-one

(4S)-3-[(5R)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidin-2-one

Conditions
ConditionsYield
With Candida antarctica B lipase In toluene at 35℃; for 120h; Solvent; Reagent/catalyst; Enzymatic reaction;A n/a
B n/a
C n/a
vinyl acetate
108-05-4

vinyl acetate

(R,S)-3-[5-(4-fluorophenyl)-5-hydroxy-pentanoyl]-4-phenyl-oxazolidin-2-one
1246853-48-4

(R,S)-3-[5-(4-fluorophenyl)-5-hydroxy-pentanoyl]-4-phenyl-oxazolidin-2-one

A

(R)-1-(4-fluorophenyl)-5-oxo-5-[(S)-2-oxo-4-phenyloxazolidin-3-yl]pentyl acetate
1246853-49-5

(R)-1-(4-fluorophenyl)-5-oxo-5-[(S)-2-oxo-4-phenyloxazolidin-3-yl]pentyl acetate

B

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one
189028-95-3

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

C

(4S)-3-[(5R)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidin-2-one

(4S)-3-[(5R)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidin-2-one

Conditions
ConditionsYield
With Candida antarctica B lipase In toluene at 35℃; for 120h; Solvent; Reagent/catalyst; Enzymatic reaction;A n/a
B n/a
C n/a
(RS)-1-(4-fluorophenyl)-5-oxo-5-[(S)-2-oxo-4-phenyloxazolidin-3-yl]pentyl acetate

(RS)-1-(4-fluorophenyl)-5-oxo-5-[(S)-2-oxo-4-phenyloxazolidin-3-yl]pentyl acetate

A

(R)-1-(4-fluorophenyl)-5-oxo-5-[(S)-2-oxo-4-phenyloxazolidin-3-yl]pentyl acetate
1246853-49-5

(R)-1-(4-fluorophenyl)-5-oxo-5-[(S)-2-oxo-4-phenyloxazolidin-3-yl]pentyl acetate

B

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one
189028-95-3

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

Conditions
ConditionsYield
With Candida rugosa lipase In aq. phosphate buffer; di-isopropyl ether at 40℃; for 120h; pH=6.2; Solvent; Reagent/catalyst; Temperature; pH-value; Concentration; Enzymatic reaction; enantioselective reaction;A n/a
B n/a
(S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione
189028-93-1

(S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione

A

(R)-1-(4-fluorophenyl)-5-oxo-5-[(S)-2-oxo-4-phenyloxazolidin-3-yl]pentyl acetate
1246853-49-5

(R)-1-(4-fluorophenyl)-5-oxo-5-[(S)-2-oxo-4-phenyloxazolidin-3-yl]pentyl acetate

B

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one
189028-95-3

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: borane-THF / dichloromethane / 6 h / 0 - 20 °C / Inert atmosphere
2: Candida rugosa lipase / di-isopropyl ether / 120 h / 35 °C / Enzymatic reaction
View Scheme
Multi-step reaction with 3 steps
1: borane-THF / dichloromethane / 6 h / 0 - 20 °C / Inert atmosphere
2: triethylamine; dmap / dichloromethane / 4 h / 0 °C
3: Candida rugosa lipase / di-isopropyl ether; aq. phosphate buffer / 120 h / 40 °C / pH 6.2 / Enzymatic reaction
View Scheme
(-)-6-(4-fluorophenyl)tetrahydro-2H-pyran-2-one
793673-93-5

(-)-6-(4-fluorophenyl)tetrahydro-2H-pyran-2-one

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one
189028-95-3

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: dmap / 1,4-dioxane / 16 h / 55 - 60 °C
2: dmap; triethylamine / tetrahydrofuran / 2 h / 4 °C
3: sodium hydride / N,N-dimethyl-formamide / 2 h / 4 - 20 °C
View Scheme
(5S)-5-(4-fluorophenyl)-5-hydroxy-N-((S)-2-hydroxy-1-phenylethyl)pentanamide

(5S)-5-(4-fluorophenyl)-5-hydroxy-N-((S)-2-hydroxy-1-phenylethyl)pentanamide

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one
189028-95-3

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dmap; triethylamine / tetrahydrofuran / 2 h / 4 °C
2: sodium hydride / N,N-dimethyl-formamide / 2 h / 4 - 20 °C
View Scheme
tert-butyl (S)-5-(4-fluorophenyl)-5-hydroxypentanoyl((S)-2-hydroxy-1-phenylethyl)carbamate

tert-butyl (S)-5-(4-fluorophenyl)-5-hydroxypentanoyl((S)-2-hydroxy-1-phenylethyl)carbamate

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one
189028-95-3

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 4 - 20℃; for 2h;800 mg
5-(4-fluorophenyl)-5-oxopentanoic acid
149437-76-3

5-(4-fluorophenyl)-5-oxopentanoic acid

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one
189028-95-3

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: sulfuric acid / 1 h / Reflux
2.1: Pinene; sodium tetrahydroborate; boron trichloride / tetrahydrofuran; 1,2-dimethoxyethane; hexane / 16 h / -15 - 4 °C
2.2: 2 h / 4 - 20 °C
3.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C
4.1: dmap / 1,4-dioxane / 16 h / 55 - 60 °C
5.1: dmap; triethylamine / tetrahydrofuran / 2 h / 4 °C
6.1: sodium hydride / N,N-dimethyl-formamide / 2 h / 4 - 20 °C
View Scheme
Multi-step reaction with 2 steps
1.1: triethylamine; pivaloyl chloride / dichloromethane / 2.5 h / 5 - 10 °C
1.2: 3 h / 15 - 45 °C
2.1: dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran / 2.33 h / -10 - -5 °C
2.2: -10 - 0 °C
View Scheme
fluorobenzene
462-06-6

fluorobenzene

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one
189028-95-3

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: aluminum (III) chloride / dichloromethane / 0.5 h / 0 °C
2.1: sulfuric acid / 1 h / Reflux
3.1: Pinene; sodium tetrahydroborate; boron trichloride / tetrahydrofuran; 1,2-dimethoxyethane; hexane / 16 h / -15 - 4 °C
3.2: 2 h / 4 - 20 °C
4.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C
5.1: dmap / 1,4-dioxane / 16 h / 55 - 60 °C
6.1: dmap; triethylamine / tetrahydrofuran / 2 h / 4 °C
7.1: sodium hydride / N,N-dimethyl-formamide / 2 h / 4 - 20 °C
View Scheme
(S)-5-(4-fluorophenyl)-5-hydroxypentanoic acid

(S)-5-(4-fluorophenyl)-5-hydroxypentanoic acid

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one
189028-95-3

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C
2: dmap / 1,4-dioxane / 16 h / 55 - 60 °C
3: dmap; triethylamine / tetrahydrofuran / 2 h / 4 °C
4: sodium hydride / N,N-dimethyl-formamide / 2 h / 4 - 20 °C
View Scheme
glutaric anhydride,
108-55-4

glutaric anhydride,

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one
189028-95-3

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: aluminum (III) chloride / dichloromethane / 0.5 h / 0 °C
2.1: sulfuric acid / 1 h / Reflux
3.1: Pinene; sodium tetrahydroborate; boron trichloride / tetrahydrofuran; 1,2-dimethoxyethane; hexane / 16 h / -15 - 4 °C
3.2: 2 h / 4 - 20 °C
4.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C
5.1: dmap / 1,4-dioxane / 16 h / 55 - 60 °C
6.1: dmap; triethylamine / tetrahydrofuran / 2 h / 4 °C
7.1: sodium hydride / N,N-dimethyl-formamide / 2 h / 4 - 20 °C
View Scheme
5-(4-fluorophenyl)-5-oxopentanoic acid methyl ester
149437-67-2

5-(4-fluorophenyl)-5-oxopentanoic acid methyl ester

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one
189028-95-3

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: Pinene; sodium tetrahydroborate; boron trichloride / tetrahydrofuran; 1,2-dimethoxyethane; hexane / 16 h / -15 - 4 °C
1.2: 2 h / 4 - 20 °C
2.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C
3.1: dmap / 1,4-dioxane / 16 h / 55 - 60 °C
4.1: dmap; triethylamine / tetrahydrofuran / 2 h / 4 °C
5.1: sodium hydride / N,N-dimethyl-formamide / 2 h / 4 - 20 °C
View Scheme
(S)-4-phenyl-2-oxazolidinone
99395-88-7

(S)-4-phenyl-2-oxazolidinone

5-(4-fluorophenyl)-5-oxopentanoic acid
149437-76-3

5-(4-fluorophenyl)-5-oxopentanoic acid

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one
189028-95-3

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

Conditions
ConditionsYield
Stage #1: 5-(4-fluorophenyl)-5-oxopentanoic acid With pivaloyl chloride; triethylamine In dichloromethane at 0 - 20℃; for 4h;
Stage #2: (S)-4-phenyl-2-oxazolidinone In N,N-dimethyl-formamide at 20℃; for 2h; Reflux;
Stage #3: With dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole In dichloromethane at 0 - 20℃; for 3h;
(S)-4-phenyl-2-oxazolidinone
99395-88-7

(S)-4-phenyl-2-oxazolidinone

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one
189028-95-3

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: triethylamine; pivaloyl chloride / dichloromethane / 2.5 h / 5 - 10 °C
1.2: 3 h / 15 - 45 °C
2.1: dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran / 2.33 h / -10 - -5 °C
2.2: -10 - 0 °C
View Scheme
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one
189028-95-3

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

(S)-3-((S)-5-(4-fluorophenyl)-5-((trimethylsilyl)oxy)-pentanoyl)-4-phenyloxazolidin-2-one

(S)-3-((S)-5-(4-fluorophenyl)-5-((trimethylsilyl)oxy)-pentanoyl)-4-phenyloxazolidin-2-one

Conditions
ConditionsYield
With triethylamine In tert-butyl methyl ether; toluene at -10 - 20℃; Inert atmosphere;95%
Stage #1: chloro-trimethyl-silane; (4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one With N-ethyl-N,N-diisopropylamine In dichloromethane at -10℃; for 1.5h;
Stage #2: With titanium tetrachloride
With N-ethyl-N,N-diisopropylamine In dichloromethane at -10℃;
4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine
70627-52-0

4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one
189028-95-3

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

C40H36F2N2O5
1185883-39-9

C40H36F2N2O5

Conditions
ConditionsYield
Stage #1: 4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine; (4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one With N-ethyl-N,N-diisopropylamine In dichloromethane at -5℃; for 2h; Inert atmosphere;
Stage #2: With titanium tetrachloride In dichloromethane at -30℃; for 2h; Inert atmosphere;
94%
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine
70627-52-0

4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one
189028-95-3

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

C43H44F2N2O5Si

C43H44F2N2O5Si

Conditions
ConditionsYield
Stage #1: chloro-trimethyl-silane; 4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine; (4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one With N-ethyl-N,N-diisopropylamine In dichloromethane at -5 - 5℃; Inert atmosphere;
Stage #2: With titanium tetrachloride In dichloromethane at -5 - 5℃; for 1h;
93%
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

N-(4-hydroxybenzylidene)-4-fluorobenzenamine
3382-63-6

N-(4-hydroxybenzylidene)-4-fluorobenzenamine

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one
189028-95-3

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

(4S)-3-[(2R,5S)-5-(4-fluorophenyl)-2-[(S)-[(4-fluorophenyl)amino]({4-[(trimethylsilyl)oxy]phenyl})methyl]-5-[(trimethylsilyl)oxy]pentanoyl]-4-phenyl-1,3-oxazolidin-2-one
272778-12-8

(4S)-3-[(2R,5S)-5-(4-fluorophenyl)-2-[(S)-[(4-fluorophenyl)amino]({4-[(trimethylsilyl)oxy]phenyl})methyl]-5-[(trimethylsilyl)oxy]pentanoyl]-4-phenyl-1,3-oxazolidin-2-one

Conditions
ConditionsYield
Stage #1: chloro-trimethyl-silane; N-(4-hydroxybenzylidene)-4-fluorobenzenamine; (4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one With N-ethyl-N,N-diisopropylamine In dichloromethane at -10 - 0℃; Inert atmosphere;
Stage #2: With titanium tetrachloride In dichloromethane at -30 - -25℃; Inert atmosphere;
66.6%
With triethylamine In dichloromethane at -20℃; Reagent/catalyst; Solvent;
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one
189028-95-3

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

(4S)-3-[(2R,5S)-5-(4-fluorophenyl)-2-[(S)-[(4-fluorophenyl)amino]({4-[(trimethylsilyl)oxy]phenyl})methyl]-5-[(trimethylsilyl)oxy]pentanoyl]-4-phenyl-1,3-oxazolidin-2-one
272778-12-8

(4S)-3-[(2R,5S)-5-(4-fluorophenyl)-2-[(S)-[(4-fluorophenyl)amino]({4-[(trimethylsilyl)oxy]phenyl})methyl]-5-[(trimethylsilyl)oxy]pentanoyl]-4-phenyl-1,3-oxazolidin-2-one

Conditions
ConditionsYield
Stage #1: (E)-(4-hydroxy-benzylidene)-(4-fluorophenyl)-amine; (4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one With N-ethyl-N,N-diisopropylamine In dichloromethane at -10 - -5℃;
Stage #2: chloro-trimethyl-silane In dichloromethane at -5℃; for 1.5h;
Stage #3: With titanium tetrachloride In dichloromethane at -30 - -25℃; for 3h;
65%
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

N-(4-hydroxybenzylidene)-4-fluorobenzenamine
3382-63-6

N-(4-hydroxybenzylidene)-4-fluorobenzenamine

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one
189028-95-3

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

C39H46F2N2O5Si2

C39H46F2N2O5Si2

Conditions
ConditionsYield
Stage #1: N-(4-hydroxybenzylidene)-4-fluorobenzenamine; (4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one With N-ethyl-N,N-diisopropylamine In dichloromethane at -10 - -5℃;
Stage #2: chloro-trimethyl-silane In dichloromethane at -5℃; for 1.5h;
Stage #3: With N,O-bis-(trimethylsilyl)-acetamide; titanium tetrachloride more than 3 stages;
65%
N-(4-hydroxybenzylidene)-4-fluorobenzenamine
3382-63-6

N-(4-hydroxybenzylidene)-4-fluorobenzenamine

chloromethyl methyl ether
107-30-2

chloromethyl methyl ether

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one
189028-95-3

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

C37H38F2N2O7

C37H38F2N2O7

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at -20 - -10℃; for 1h; Temperature; Reagent/catalyst;64.5%
tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one
189028-95-3

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

C26H34FNO4Si
937798-07-7

C26H34FNO4Si

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 80℃; Reagent/catalyst; Temperature;62%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 1h;42 g
4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine
70627-52-0

4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one
189028-95-3

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

C40H36F2N2O5

C40H36F2N2O5

Conditions
ConditionsYield
With titanium(IV) isopropylate; titanium tetrachloride; N-ethyl-N,N-diisopropylamine In dichloromethane at -30 - -20℃; for 5h;60.9%
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

N,O-bis-(trimethylsilyl)-acetamide
10416-59-8

N,O-bis-(trimethylsilyl)-acetamide

N-(4-hydroxybenzylidene)-4-fluorobenzenamine
3382-63-6

N-(4-hydroxybenzylidene)-4-fluorobenzenamine

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one
189028-95-3

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

(4S)-3-[(2R,5S)-5-(4-fluorophenyl)-2-[(S)-[(4-fluorophenyl)amino]({4-[(trimethylsilyl)oxy]phenyl})methyl]-5-[(trimethylsilyl)oxy]pentanoyl]-4-phenyl-1,3-oxazolidin-2-one
272778-12-8

(4S)-3-[(2R,5S)-5-(4-fluorophenyl)-2-[(S)-[(4-fluorophenyl)amino]({4-[(trimethylsilyl)oxy]phenyl})methyl]-5-[(trimethylsilyl)oxy]pentanoyl]-4-phenyl-1,3-oxazolidin-2-one

Conditions
ConditionsYield
Stage #1: chloro-trimethyl-silane; N-(4-hydroxybenzylidene)-4-fluorobenzenamine; (4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one With N-ethyl-N,N-diisopropylamine In dichloromethane at -10 - -5℃; for 1h;
Stage #2: With titanium tetrachloride In dichloromethane at -30℃; for 20h;
Stage #3: N,O-bis-(trimethylsilyl)-acetamide
60%
N-{(1E)-[2-(benzyloxy)-4-bromophenyl]methylene}-N-phenylamine
914777-35-8

N-{(1E)-[2-(benzyloxy)-4-bromophenyl]methylene}-N-phenylamine

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one
189028-95-3

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

(S)-3-[(2R,5S)-2-[(S)-(2-benzyloxy-4-bromo-phenyl)-phenylamino-methyl]-5-(4-fluoro-phenyl)-5-hydroxy-pentanoyl]-4-phenyl-oxazolidin-2-one
914777-36-9

(S)-3-[(2R,5S)-2-[(S)-(2-benzyloxy-4-bromo-phenyl)-phenylamino-methyl]-5-(4-fluoro-phenyl)-5-hydroxy-pentanoyl]-4-phenyl-oxazolidin-2-one

Conditions
ConditionsYield
Stage #1: (4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one With chloro-trimethyl-silane; N-ethyl-N,N-diisopropylamine In dichloromethane at -45 - -20℃; for 1h;
Stage #2: With titanium tetrachloride In dichloromethane at -35 - -30℃; for 0.75h;
Stage #3: N-{(1E)-[2-(benzyloxy)-4-bromophenyl]methylene}-N-phenylamine With acetic acid more than 3 stages;
51%
Stage #1: (4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one With chloro-trimethyl-silane; N-ethyl-N,N-diisopropylamine In dichloromethane at -45 - -20℃; for 1h;
Stage #2: With titanium tetrachloride In dichloromethane at -45 - -30℃; for 1.08333h;
Stage #3: N-{(1E)-[2-(benzyloxy)-4-bromophenyl]methylene}-N-phenylamine With acetic acid; tartaric acid more than 3 stages;
51%
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one
189028-95-3

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

C10(13)C6H18FNOSi

C10(13)C6H18FNOSi

C30(13)C6H38F2N2O5Si

C30(13)C6H38F2N2O5Si

Conditions
ConditionsYield
With titanium tetrachloride In dichloromethane at -35 - -30℃; for 3h;
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one
189028-95-3

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-hydroxypropyl]-4-([12C6]-4-hydroxyphenyl)-2-azetidinone

1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-hydroxypropyl]-4-([12C6]-4-hydroxyphenyl)-2-azetidinone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: TiCl4 / CH2Cl2 / 3 h / -35 - -30 °C
2.1: 995 mg / CH2Cl2 / 0.5 h / Heating
3.1: BSA / CH2Cl2 / 0.25 h / 20 °C
3.2: TBAF*3H2O / CH2Cl2 / 90 h / 0 °C
3.3: 90 percent / aq. H2SO4 / propan-2-ol / 1 h
View Scheme
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one
189028-95-3

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

C33(13)C6H46F2N2O5Si2
438624-70-5

C33(13)C6H46F2N2O5Si2

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: TiCl4 / CH2Cl2 / 3 h / -35 - -30 °C
2: 995 mg / CH2Cl2 / 0.5 h / Heating
View Scheme
benzyl bromide
100-39-0

benzyl bromide

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one
189028-95-3

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

(4S)-3-[(5S)-5-(benzyloxy)-5-(4-fluorophenyl)pentanoyl]-4-phenyl-1,3-oxazolidin-2-one
851860-27-0

(4S)-3-[(5S)-5-(benzyloxy)-5-(4-fluorophenyl)pentanoyl]-4-phenyl-1,3-oxazolidin-2-one

Conditions
ConditionsYield
With sodium hydride In DMF (N,N-dimethyl-formamide) at 0 - 20℃; for 0.666667h;
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

4-{[(1E)-(4-iodophenyl)methylene]amino}phenol
3230-41-9

4-{[(1E)-(4-iodophenyl)methylene]amino}phenol

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one
189028-95-3

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

C40H48FIN2O5Si2

C40H48FIN2O5Si2

Conditions
ConditionsYield
Stage #1: 4-{[(1E)-(4-iodophenyl)methylene]amino}phenol; (4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one With N-ethyl-N,N-diisopropylamine In dichloromethane at -5 - 0℃;
Stage #2: chloro-trimethyl-silane In dichloromethane at -25 - 0℃; for 1h;
Stage #3: With titanium tetrachloride; sodium hydrogensulfite; rochelle salt more than 3 stages;
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

4-({(1E)-[2-(allyloxy)-4-bromophenyl]methylene}amino)phenol
1078641-31-2

4-({(1E)-[2-(allyloxy)-4-bromophenyl]methylene}amino)phenol

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one
189028-95-3

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

(4S)-3-{(2R,5S)-2-{(S)-[2-(allyloxy)-4-bromophenyl][(4-hydroxyphenyl)amino]methyl}-5-(4-fluorophenyl)-5-[(trimethylsilyl)oxy]pentanoyl}-4-phenyl-1,3-oxazolidin-2-one
1078641-32-3

(4S)-3-{(2R,5S)-2-{(S)-[2-(allyloxy)-4-bromophenyl][(4-hydroxyphenyl)amino]methyl}-5-(4-fluorophenyl)-5-[(trimethylsilyl)oxy]pentanoyl}-4-phenyl-1,3-oxazolidin-2-one

Conditions
ConditionsYield
Stage #1: chloro-trimethyl-silane; 4-({(1E)-[2-(allyloxy)-4-bromophenyl]methylene}amino)phenol; (4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one With N-ethyl-N,N-diisopropylamine In dichloromethane at -30 - 0℃; for 1h;
Stage #2: With Rochelle's salt; sodium hydrogensulfite; acetic acid; titanium tetrachloride In dichloromethane; water at -30 - 20℃; Cooling with ice/salt;
Stage #3: With N,O-bis-(trimethylsilyl)-acetamide at 45℃; for 0.5h;
Reaxys ID: 19845323

Reaxys ID: 19845323

N-(4-hydroxybenzylidene)-4-fluorobenzenamine
3382-63-6

N-(4-hydroxybenzylidene)-4-fluorobenzenamine

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one
189028-95-3

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

Reaxys ID: 19845322

Reaxys ID: 19845322

Conditions
ConditionsYield
With titanium tetrachloride; N-ethyl-N,N-diisopropylamine In dichloromethane
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one
189028-95-3

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

ezetemibe
163222-33-1

ezetemibe

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / -10 °C
2.1: titanium tetrachloride / dichloromethane / 0.75 h / -40 °C
2.2: 19.5 h / -40 - -35 °C
3.1: acetic acid / dichloromethane / 1 h
3.2: 1 h / 0 °C
3.3: 1 h / 20 °C
4.1: toluene / 3 h / 90 °C
4.2: 14 h / 50 °C
5.1: hydrogenchloride; water; acetic acid; iron / ethanol / 0.5 h / 0 - 20 °C
6.1: sodium nitrite; sulfuric acid / N,N-dimethyl-formamide; water / 1.5 h / 0 °C
6.2: 0.42 h / 20 - 90 °C
View Scheme
Multi-step reaction with 2 steps
1.1: N-ethyl-N,N-diisopropylamine; chloro-trimethyl-silane; titanium tetrachloride / dichloromethane / 2 h / -30 - -25 °C
1.2: 2 h / Reflux
2.1: bis-(trimethylsilyl)acetamide; tetrabutyl ammonium fluoride / tert-butyl methyl ether / 1.5 h / 20 °C
2.2: 0.5 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: triethylamine / dichloromethane / -20 °C
2: H-ZSM-5 molecular sieve / -30 °C
3: perchloric acid / 3 h / 40 °C
View Scheme
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one
189028-95-3

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

C36H37F2N3O6Si

C36H37F2N3O6Si

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / -10 °C
2.1: titanium tetrachloride / dichloromethane / 0.75 h / -40 °C
2.2: 19.5 h / -40 - -35 °C
View Scheme
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one
189028-95-3

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

(4S)-phenyl-3-[(5S)-(4-fluorophenyl)-(2R)-[(1S)-(4-fluorophenylamino)-1-(4-nitrophenyl)methyl]-5-hydroxypentanoyl]oxazolidin-2-one
1354716-96-3

(4S)-phenyl-3-[(5S)-(4-fluorophenyl)-(2R)-[(1S)-(4-fluorophenylamino)-1-(4-nitrophenyl)methyl]-5-hydroxypentanoyl]oxazolidin-2-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / -10 °C
2.1: titanium tetrachloride / dichloromethane / 0.75 h / -40 °C
2.2: 19.5 h / -40 - -35 °C
3.1: acetic acid / dichloromethane / 1 h
3.2: 1 h / 0 °C
3.3: 1 h / 20 °C
View Scheme
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one
189028-95-3

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

1-(4-fluorophenyl)-(3R)-[(3S)-(4-fluorophenyl)-3-trimethylsilyloxypropyl]-(4S)-(4-nitrophenyl)azetidin-2-one
1354716-97-4

1-(4-fluorophenyl)-(3R)-[(3S)-(4-fluorophenyl)-3-trimethylsilyloxypropyl]-(4S)-(4-nitrophenyl)azetidin-2-one

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / -10 °C
2.1: titanium tetrachloride / dichloromethane / 0.75 h / -40 °C
2.2: 19.5 h / -40 - -35 °C
3.1: acetic acid / dichloromethane / 1 h
3.2: 1 h / 0 °C
3.3: 1 h / 20 °C
4.1: toluene / 3 h / 90 °C
4.2: 14 h / 50 °C
View Scheme
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one
189028-95-3

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

(4S)-(4-aminophenyl)-1-(4-fluorophenyl)-(3R)-[(3S)-(4-fluorophenyl)-3-hydroxypropyl]azetidin-2-one
1354716-98-5

(4S)-(4-aminophenyl)-1-(4-fluorophenyl)-(3R)-[(3S)-(4-fluorophenyl)-3-hydroxypropyl]azetidin-2-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / -10 °C
2.1: titanium tetrachloride / dichloromethane / 0.75 h / -40 °C
2.2: 19.5 h / -40 - -35 °C
3.1: acetic acid / dichloromethane / 1 h
3.2: 1 h / 0 °C
3.3: 1 h / 20 °C
4.1: toluene / 3 h / 90 °C
4.2: 14 h / 50 °C
5.1: hydrogenchloride; water; acetic acid; iron / ethanol / 0.5 h / 0 - 20 °C
View Scheme

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