Shandong Mopai Biotechnology Co., LTD is a leading manufacturer and supplier of chemicals in China. We develop produce and distribute high quality pharmaceuticals, intermediates, special chemicals and OLED intermediates and other fine chemicals. W
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inquiry(2R,4S)-5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-Methylpentanoic acid CAS 1012341-50-2 Company profile Wuhan Fortuna Chemical Co.,Ltd established in 2006, is a big integrative chemical enterprise being engaged in Pharmaceuti
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inquiry(2R,4S)-5-(Biphenyl-4-yl)-4-[(tert-butoxycarbonyl)amino]-2-methylpentanoic acid CAS No.:1012341-50-2 Name: (2R,4S)-5-(Biphenyl-4-yl)-4-[(tert-butoxycarbonyl)amino]-2-methylpentanoic acid Molecular Structu
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inquiry1. 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
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inquiryCangzhou Enke Pharma Tech Co.,ltd. is located in Cangzhou City, Hebei province ,where is a famous petroleum chemical industry city in China. Enke Pharma a high-tech enterprise ,and we are dedicated to developing and manufacturing new ap
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inquiryHebei yanxi chemical co., LTD is a professional research, development and production of lead acetate benzene acetamide enterprise backbone members by local well-known entrepreneurs and professional senior engineers in the party's "low carb
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inquiryProduct Description Product website: http://www.finerchem.com/pro01en/id/942.html Product Name (2R,4S)-5-(Biphenyl-4-yl)-4-[(tert-butoxycarbonyl)amino]-2-methylpentanoic acid
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inquiry(2R,4S)-5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-Methylpentanoic acid Basic information Product Name: (2R,4S)-5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-Methylpentanoic acid Synonyms: (2R,4S)-5-([1,1'
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inquiryLIDE PHARMACEUTICALS LIMITED is a professional chemicals and APIs leading manufacturer in China. Our core business line covers APIs, Intermediates, Herb extract, etc.
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inquiryOur 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
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inquiryOur company was built in 2009 with an ISO certificate.In the past 5 years, we have grown up as a famous fine chemicals supplier in China and we had established stable business relationships with Samsung,LG,Merck,Thermo Fisher Scientific and so on.O
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inquiry1. Product advantages ♦ High purity, all above 98.5%, no impurities after dissolution ♦ We will test each batch to ensure quality ♦ OEM and private brand services designed for free ♦ Various cap colors available ♦ W
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inquiryName: 2R,4S)-5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid Synonyms: (2r,4s)-5-(biphenyl-4-yl)-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid CAS:1012341-50-2 MF: C23H29NO4 Appearance: white powder Stor
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inquiryAdvantages: Hubei XinRunde Chemical Co., Ltd is a renowned pharmaceutical manufacturer. We can offer high quality products at competitive price in quick delivery with 100% custom pass guaranteed. Never stop striving to offer our best service is
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inquiryHanways Chempharm Co., Limited, the former is Hubei Hanways Pharchem CO.,Limited, set up in 2009 in Wuhan, China. We specialize in sourcing and supplying APIs, pharmaceutical intermediates, and fine chemicals for worldwide markets. The founder has d
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inquiryHangzhou 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
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inquiry(2R,4S)-5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-Methylpentanoic acid Chemical Properties Boiling point 582.6±50.0 °C(Predicted) density 1.115±0.06 g/cm3(Predicted) storage temp. 2-8°C pka 4 +
Cas:1012341-50-2
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inquiryOur 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
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inquiry(2R,4S)-5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-Methylpentanoic acid CAS:1012341-50-2 Qingdao Belugas Import and Export Co., Ltd. is a scientific and technological company integrating research and development, production and tr
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inquiryHello, 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
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inquiry1,we produce and sell good chemicals around the world. 2,our success rate is about 95%. this means, if customer order is accepted, the probability that the customer will obtain the ordered substances, is 95%. 3,our staff consists of highly qualifie
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inquiryHenan 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
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inquiryAppearance:white or light yellow crystalline powder Storage:Store in a cool,dry place and keep away from direct strong light Package:As customer request Application:Used for research and industrial manufacture. Transportation:By
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inquiryHangzhou 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
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inquiryCompany Introduction 1. Established in 2005, with two independent business divisions: Fine chemicals division; Pharmaceutical division. 2. Main product: Optical brightener Textile auxiliary Dye stuff Pigments
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inquiry(2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid
Conditions | Yield |
---|---|
Stage #1: C33H38N2O5 With dihydrogen peroxide In tetrahydrofuran at 0℃; for 0.5h; Stage #2: With lithium hydroxide at 25 - 30℃; for 3h; | 95% |
(2E,4R)-5-{[1,1'-biphenyl]-4-yl}-4-{[(tert-butoxy)carbonyl]amino}-2-methylpent-2-enoic acid
(2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid
Conditions | Yield |
---|---|
With ammonium formate; nickel(II) acetate tetrahydrate; (R,R)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine In ethanol at 55℃; for 8h; Temperature; | 91.9% |
With hydrogen under 15001.5 - 18751.9 Torr; | 90% |
With hydrogen; diiodo(p-cymene)ruthenium(II) dimer; (SP,S′P)-1,1′-bis[bis(4-methoxy-3,5-dimethylphenyl)phosphino]-2,2′-bis[(R)-α-(dimethylamino)benzyl]ferrocene In ethanol at 40℃; under 15001.5 Torr; for 6h; Product distribution / selectivity; | 86.9% |
(2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid
Conditions | Yield |
---|---|
Stage #1: C33H38N2O5 With dihydrogen peroxide In tetrahydrofuran at 0℃; for 0.5h; Stage #2: With lithium hydroxide In tetrahydrofuran; water at 20 - 25℃; for 3h; | 90% |
(3R,5S)-5-biphenyl-4-ylmethyl-3-methyl-2-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester
(2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid
Conditions | Yield |
---|---|
With sodium hydroxide at 60℃; Reagent/catalyst; | 86% |
Stage #1: (3R,5S)-5-biphenyl-4-ylmethyl-3-methyl-2-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester With lithium hydroxide In tetrahydrofuran; water at 20℃; for 1h; Stage #2: With phosphoric acid In tetrahydrofuran; water Product distribution / selectivity; |
di-tert-butyl dicarbonate
(2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid
Conditions | Yield |
---|---|
Stage #1: (R)-2-methyl-4-hydroxyimino-5-(4-biphenyl)pentanoic acid With ((+)-(1R)-[1,1'-binaphthalene]-2,2'-diylbis[diphenylphosphine-κP])chloro[(1,2,3,4,5,6-η)-1-methyl-4-(1-methylethyl)benzene]ruthenium(1+) chloride; hydrogen In methanol at 40℃; under 30003 Torr; Autoclave; Stage #2: di-tert-butyl dicarbonate With lithium hydroxide Reflux; diastereoselective reaction; | 80% |
(R)-5-(biphenyl-4-yl)-4-tert-butoxycarbonylamino-2-methylpent-2-enoic acid
cyclohexylamine
A
(2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid
Conditions | Yield |
---|---|
Stage #1: (R)-5-(biphenyl-4-yl)-4-tert-butoxycarbonylamino-2-methylpent-2-enoic acid With palladium 10% on activated carbon; hydrogen In ethanol; water at 40℃; under 3750.38 Torr; for 3h; Stage #2: cyclohexylamine In Isopropyl acetate at 70℃; | A 58% B 10% |
(2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid
Conditions | Yield |
---|---|
With (S)-1-(1-Naphthyl)ethylamine In methanol at 60℃; for 1h; Temperature; | 37% |
With (S)-1-phenyl-ethylamine In ethanol at 20℃; for 2h; |
(2E,4R)-5-{[1,1'-biphenyl]-4-yl}-4-{[(tert-butoxy)carbonyl]amino}-2-methylpent-2-enoic acid
B
(2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid
Conditions | Yield |
---|---|
With diiodo(p-cymene)ruthenium(II) dimer; (SP,S′P)-1,1′-bis[bis(4-methoxy-3,5-dimethylphenyl)phosphino]-2,2′-bis[(R)-α-(dimethylamino)benzyl]ferrocene; hydrogen In ethanol at 75℃; under 22502.3 Torr; | A 5.3% B 93.66 %Chromat. |
With diiodo(p-cymene)ruthenium(II) dimer; (SP,S′P)-1,1′-bis[bis(4-methoxy-3,5-dimethylphenyl)phosphino]-2,2′-bis[(R)-α-(dimethylamino)benzyl]ferrocene; hydrogen In dichloromethane; water at 60℃; under 45004.5 Torr; for 16h; Autoclave; Ionic liquid; Inert atmosphere; | A n/a B n/a |
(2R,4S)-5-([1,1'-biphenyl]-4-yl)-4-amino-2-methylpentanoic acid hydrochloride
di-tert-butyl dicarbonate
(2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid
Conditions | Yield |
---|---|
Stage #1: (2R,4S)-5-([1,1'-biphenyl]-4-yl)-4-amino-2-methylpentanoic acid hydrochloride; di-tert-butyl dicarbonate With potassium carbonate In water; isopropyl alcohol at 20℃; for 1h; Stage #2: With phosphoric acid In water; isopropyl alcohol Product distribution / selectivity; |
(3R,5S)-5-biphenyl-4-ylmethyl-3-methyl-2-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester
B
(2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: sodium hydride; potassium hexamethylsilazane / toluene / 1 h / -15 °C 1.2: 0.5 h / -15 °C 1.3: 1 h / 20 °C 2.1: water; lithium hydroxide / tetrahydrofuran / 20 h / 20 °C 3.1: triethylamine; hydrogen / 5% rhodium-on-charcoal / Isopropyl acetate / 20 °C / 760.05 Torr View Scheme | |
Multi-step reaction with 3 steps 1.1: sodium hydride; potassium hexamethylsilazane / toluene; mineral oil / 1 h / -15 °C 1.2: 0.5 h / -15 °C 1.3: 1 h / 20 °C 2.1: lithium hydroxide; water / tetrahydrofuran / 20 h / 20 °C 3.1: hydrogen; triethylamine; 10% Pt/activated carbon / Isopropyl acetate / 20 °C / 760.05 Torr View Scheme |
(R)-5-biphenyl-4-ylmethyl-3-methylene-2-oxo-pyrrolidine-1-carboxylic acid tert-butylester
B
(2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sodium hydrogencarbonate / tetrakis(triphenylphosphine) palladium(0); triphenylphosphine / xylene / Reflux 2: water; lithium hydroxide / tetrahydrofuran / 20 h / 20 °C 3: triethylamine; hydrogen / 5% rhodium-on-charcoal / Isopropyl acetate / 20 °C / 760.05 Torr View Scheme | |
Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium(0); triphenylphosphine; sodium hydrogencarbonate / 5,5-dimethyl-1,3-cyclohexadiene / Reflux 2: lithium hydroxide; water / tetrahydrofuran / 20 h / 20 °C 3: hydrogen; triethylamine; 10% Pt/activated carbon / Isopropyl acetate / 20 °C / 760.05 Torr View Scheme |
(Z)-(R)-5-biphenyl-4-yl-4-tert-butoxycarbonylamino-2-methylpent-2-enoic acid
B
(2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid
Conditions | Yield |
---|---|
With hydrogen; triethylamine; 5% rhodium-on-charcoal In Isopropyl acetate at 20℃; under 760.051 Torr; Product distribution / selectivity; | |
With hydrogen; triethylamine; palladium 10% on activated carbon In Isopropyl acetate at 20℃; under 760.051 Torr; Product distribution / selectivity; | |
With palladium 10% on activated carbon; hydrogen; triethylamine In Isopropyl acetate at 20℃; under 760.051 Torr; Reagent/catalyst; | |
With 10% Pt/activated carbon; hydrogen; triethylamine In Isopropyl acetate at 20℃; under 760.051 Torr; Reagent/catalyst; |
(R)-5-biphenyl-4-ylmethyl-3-methyl-2-oxo-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester
B
(2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: water; lithium hydroxide / tetrahydrofuran / 20 h / 20 °C 2: triethylamine; hydrogen / 5% rhodium-on-charcoal / Isopropyl acetate / 20 °C / 760.05 Torr View Scheme |
(2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: bis(dicyclopentadiene)rhodium tetrafluoroborate; C52H44N2O2P2; hydrogen / methanol / 50 °C / Autoclave 2: pyridine / dichloromethane / 0.17 h / -17 - -15 °C 3: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / toluene / 80 °C / Inert atmosphere 4: lithium hydroxide; water / ethanol / 70 °C View Scheme |
(2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: pyridine / dichloromethane / 0.17 h / -17 - -15 °C 2: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / toluene / 80 °C / Inert atmosphere 3: lithium hydroxide; water / ethanol / 70 °C View Scheme |
(2S,4S)-5-biphenyl-4-yl-4-tert-butoxycarbonylamino-2-methylpentanoic acid ethyl ester
(2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid
Conditions | Yield |
---|---|
With water; lithium hydroxide In ethanol at 70℃; |
N-(tert-butoxycarbonyl)-D-tyrosine
(2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: benzotriazol-1-ol; triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C / 37.5 - 75.01 Torr 2: lithium aluminium tetrahydride / diethyl ether / 0 °C 3: dichloromethane / 20 - 25 °C 4: bis(dicyclopentadiene)rhodium tetrafluoroborate; C52H44N2O2P2; hydrogen / methanol / 50 °C / Autoclave 5: pyridine / dichloromethane / 0.17 h / -17 - -15 °C 6: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / toluene / 80 °C / Inert atmosphere 7: lithium hydroxide; water / ethanol / 70 °C View Scheme |
tert-butyl (R)-3-(4-hydroxyphenyl)-1-[methoxy(methyl)amino]-1-oxopropan-2-ylcarbamate
(2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: lithium aluminium tetrahydride / diethyl ether / 0 °C 2: dichloromethane / 20 - 25 °C 3: bis(dicyclopentadiene)rhodium tetrafluoroborate; C52H44N2O2P2; hydrogen / methanol / 50 °C / Autoclave 4: pyridine / dichloromethane / 0.17 h / -17 - -15 °C 5: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / toluene / 80 °C / Inert atmosphere 6: lithium hydroxide; water / ethanol / 70 °C View Scheme |
(2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: dichloromethane / 20 - 25 °C 2: bis(dicyclopentadiene)rhodium tetrafluoroborate; C52H44N2O2P2; hydrogen / methanol / 50 °C / Autoclave 3: pyridine / dichloromethane / 0.17 h / -17 - -15 °C 4: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / toluene / 80 °C / Inert atmosphere 5: lithium hydroxide; water / ethanol / 70 °C View Scheme |
phenylboronic acid
(2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid
Conditions | Yield |
---|---|
With dipotassium hydrogenphosphate; formic acid; palladium diacetate In water at 25 - 45℃; for 6h; Inert atmosphere; | 8 g |
(2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: sodium tetrahydroborate / ethanol / 4 h / 25 - 35 °C 2: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; sodium bromide; sodium hypochlorite solution / ethyl acetate; water / 2 h 3: ethyl acetate / 2 h / 25 - 35 °C 4: lithium hydroxide / ethanol; water / 3 h / 50 - 85 °C 5: diiodo(p-cymene)ruthenium(II) dimer; (α,α)2,2'-bis(α-N,N-dimethylaminophenylmethyl)-(S,S)-1,1'-bis-[di(3,5-dimethyl-4-methoxyphenyl)-phosphino]ferrocene; hydrogen / methanol / 7 h / 55 - 65 °C / 11251.1 - 15001.5 Torr / Autoclave; Inert atmosphere 6: formic acid; dipotassium hydrogenphosphate; palladium diacetate / water / 6 h / 25 - 45 °C / Inert atmosphere View Scheme |
(2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; sodium bromide; sodium hypochlorite solution / ethyl acetate; water / 2 h 2: ethyl acetate / 2 h / 25 - 35 °C 3: lithium hydroxide / ethanol; water / 3 h / 50 - 85 °C 4: diiodo(p-cymene)ruthenium(II) dimer; (α,α)2,2'-bis(α-N,N-dimethylaminophenylmethyl)-(S,S)-1,1'-bis-[di(3,5-dimethyl-4-methoxyphenyl)-phosphino]ferrocene; hydrogen / methanol / 7 h / 55 - 65 °C / 11251.1 - 15001.5 Torr / Autoclave; Inert atmosphere 5: formic acid; dipotassium hydrogenphosphate; palladium diacetate / water / 6 h / 25 - 45 °C / Inert atmosphere View Scheme |
(2R)-2-amino-3-(4-bromophenyl)propanoic acid
(2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: thiophosgene / methanol / 4 h / 60 - 65 °C 1.2: 6 h / 25 - 35 °C 2.1: sodium tetrahydroborate / ethanol / 4 h / 25 - 35 °C 3.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; sodium bromide; sodium hypochlorite solution / ethyl acetate; water / 2 h 4.1: ethyl acetate / 2 h / 25 - 35 °C 5.1: lithium hydroxide / ethanol; water / 3 h / 50 - 85 °C 6.1: diiodo(p-cymene)ruthenium(II) dimer; (α,α)2,2'-bis(α-N,N-dimethylaminophenylmethyl)-(S,S)-1,1'-bis-[di(3,5-dimethyl-4-methoxyphenyl)-phosphino]ferrocene; hydrogen / methanol / 7 h / 55 - 65 °C / 11251.1 - 15001.5 Torr / Autoclave; Inert atmosphere 7.1: formic acid; dipotassium hydrogenphosphate; palladium diacetate / water / 6 h / 25 - 45 °C / Inert atmosphere View Scheme |
di-tert-butyl dicarbonate
(2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: thiophosgene / methanol / 4 h / 60 - 65 °C 1.2: 6 h / 25 - 35 °C 2.1: sodium tetrahydroborate / ethanol / 4 h / 25 - 35 °C 3.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; sodium bromide; sodium hypochlorite solution / ethyl acetate; water / 2 h 4.1: ethyl acetate / 2 h / 25 - 35 °C 5.1: lithium hydroxide / ethanol; water / 3 h / 50 - 85 °C 6.1: diiodo(p-cymene)ruthenium(II) dimer; (α,α)2,2'-bis(α-N,N-dimethylaminophenylmethyl)-(S,S)-1,1'-bis-[di(3,5-dimethyl-4-methoxyphenyl)-phosphino]ferrocene; hydrogen / methanol / 7 h / 55 - 65 °C / 11251.1 - 15001.5 Torr / Autoclave; Inert atmosphere 7.1: formic acid; dipotassium hydrogenphosphate; palladium diacetate / water / 6 h / 25 - 45 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1: dmap / 20 °C 2: sodium hydroxide / 60 °C View Scheme |
tert-butyl [(2R)-1-(4-bromophenyl)-3-oxypropan-2-yl] carbamate
(2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: ethyl acetate / 2 h / 25 - 35 °C 2: lithium hydroxide / ethanol; water / 3 h / 50 - 85 °C 3: diiodo(p-cymene)ruthenium(II) dimer; (α,α)2,2'-bis(α-N,N-dimethylaminophenylmethyl)-(S,S)-1,1'-bis-[di(3,5-dimethyl-4-methoxyphenyl)-phosphino]ferrocene; hydrogen / methanol / 7 h / 55 - 65 °C / 11251.1 - 15001.5 Torr / Autoclave; Inert atmosphere 4: formic acid; dipotassium hydrogenphosphate; palladium diacetate / water / 6 h / 25 - 45 °C / Inert atmosphere View Scheme |
ethyl (2E, 4R)-5-(4-bromophenyl)-4-[(tert-butoxycarbonyl) amino]-2-methylpent-enoate
(2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: lithium hydroxide / ethanol; water / 3 h / 50 - 85 °C 2: diiodo(p-cymene)ruthenium(II) dimer; (α,α)2,2'-bis(α-N,N-dimethylaminophenylmethyl)-(S,S)-1,1'-bis-[di(3,5-dimethyl-4-methoxyphenyl)-phosphino]ferrocene; hydrogen / methanol / 7 h / 55 - 65 °C / 11251.1 - 15001.5 Torr / Autoclave; Inert atmosphere 3: formic acid; dipotassium hydrogenphosphate; palladium diacetate / water / 6 h / 25 - 45 °C / Inert atmosphere View Scheme |
(2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: diiodo(p-cymene)ruthenium(II) dimer; (α,α)2,2'-bis(α-N,N-dimethylaminophenylmethyl)-(S,S)-1,1'-bis-[di(3,5-dimethyl-4-methoxyphenyl)-phosphino]ferrocene; hydrogen / methanol / 7 h / 55 - 65 °C / 11251.1 - 15001.5 Torr / Autoclave; Inert atmosphere 2: formic acid; dipotassium hydrogenphosphate; palladium diacetate / water / 6 h / 25 - 45 °C / Inert atmosphere View Scheme |
(3R,5S)-5-({[1,1'-biphenyl]-4-yl}methyl)-3-methylpyrrolidin-2-one
(2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: dmap / 20 °C 2: sodium hydroxide / 60 °C View Scheme |
(2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: triphenylphosphine; bromine / dichloromethane / 0 - 20 °C 2.1: magnesium; iodine / tetrahydrofuran / 0 - 60 °C / Inert atmosphere 2.2: 0 - 20 °C / Inert atmosphere 3.1: dmap / 20 °C 4.1: sodium hydroxide / 60 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: triethylamine / dichloromethane / 20 °C 2.1: magnesium; iodine / tetrahydrofuran / 0 - 60 °C / Inert atmosphere 2.2: 0 - 20 °C / Inert atmosphere 3.1: dmap / 20 °C 4.1: sodium hydroxide / 60 °C View Scheme |
(2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: magnesium; iodine / tetrahydrofuran / 0 - 60 °C / Inert atmosphere 1.2: 0 - 20 °C / Inert atmosphere 2.1: dmap / 20 °C 3.1: sodium hydroxide / 60 °C View Scheme |
(2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid
Conditions | Yield |
---|---|
With dmap; copper diacetate In acetonitrile at 80℃; Schlenk technique; Sealed tube; | 99% |
(2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid
ethanol
(2R,4S)-5-([1,1'-biphenyl]-4-yl)-4-amino-2-methylpentanoic acid ethyl ester hydrochloride
Conditions | Yield |
---|---|
With thionyl chloride | 98% |
With thionyl chloride at 20 - 50℃; | 96% |
With thionyl chloride at 60℃; | 96% |
(2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid
(2R,4S)-5-([1,1'-biphenyl]-4-yl)-4-amino-2-methylpentanoic acid ethyl ester hydrochloride
Conditions | Yield |
---|---|
With thionyl chloride In ethanol at 60℃; for 1h; | 96.5% |
With thiophosgene In ethanol at 70 - 75℃; for 3h; | |
With thionyl chloride In ethanol; tert-butyl methyl ether at 60 - 70℃; for 3h; |
(2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid
6-(N,N-dimethylamino)-1-hexanol
Conditions | Yield |
---|---|
With thionyl chloride In dichloromethane for 1h; Reflux; | 89.7% |
(2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid
benzyl bromide
(2R,4S)-5-biphenyl-4-yl-4-tert-butoxycarbonylamino-2-methyl-pentanoic acid benzyl ester
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile at 60℃; for 0.5h; | 88.7% |
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 2h; |
2-(N,N-dimethylamino)ethanol
(2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid
Conditions | Yield |
---|---|
With thionyl chloride In dichloromethane for 1h; Reflux; | 88.7% |
(2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid
ethanol
(2R,4S)-4-amino-5-biphenyl-4-yl-2-methylpentanoic acid ethyl ester
Conditions | Yield |
---|---|
With thionyl chloride at 78℃; Temperature; | 88% |
With thionyl chloride at 40℃; for 4h; | 87.8% |
With thionyl chloride at 0 - 50℃; for 8h; Reagent/catalyst; Temperature; | 0.7 g |
(2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid
2-(Diethylamino)ethanol
Conditions | Yield |
---|---|
With thionyl chloride In dichloromethane for 1h; Reflux; | 87.2% |
(2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid
N-(2-Hydroxyethyl)phthalimide
Conditions | Yield |
---|---|
Stage #1: (2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid With dmap; dicyclohexyl-carbodiimide In dichloromethane for 0.5h; Stage #2: N-(2-Hydroxyethyl)phthalimide In dichloromethane for 4h; Reflux; | 85.7% |
(2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid
ethanol
ethyl (2R,4S)-5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)amino)-2-methylpentanoate
Conditions | Yield |
---|---|
With thionyl chloride for 10h; Reflux; | 85% |
(2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid
N-benzyl-2-(ethylamino)ethanol
Conditions | Yield |
---|---|
With thionyl chloride In dichloromethane for 11h; Reflux; | 83.2% |
(2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid
isopropyl alcohol
Conditions | Yield |
---|---|
With thionyl chloride at 85℃; for 9h; | 80% |
With thionyl chloride at 0 - 80℃; for 8h; | 0.75 g |
(2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid
N-pentanoyl-N-[[2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]-methyl]-(L)-valine
Conditions | Yield |
---|---|
Stage #1: (2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid; D-lysine; N-pentanoyl-N-[[2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]-methyl]-(L)-valine With water; sodium hydroxide In acetone at 20℃; for 1h; Stage #2: With calcium chloride In acetone for 3h; | 75.5% |
methanol
(2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid
Conditions | Yield |
---|---|
With thionyl chloride at 40℃; for 4h; Temperature; Concentration; | 75% |
(2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid
triethylamine
Conditions | Yield |
---|---|
In tetrahydrofuran for 6h; | 64.5% |
(2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid
triethylamine
Conditions | Yield |
---|---|
In tetrahydrofuran for 6h; | 61.5% |
(2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid
methanesulfonamide
((1S,3R)-1-biphenyl-4-ylmethyl-4-methanesulfonylamino-3-methyl-4-oxo-butyl)-carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; | 55% |
(2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid
ethanol
(2R,4S)-4-amino-5-biphenyl-4-yl-2-methylpentanoic acid ethyl ester hydrobromide
Conditions | Yield |
---|---|
With dibromo sulfoxide at 65℃; for 1.5h; |
(2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid
ethanol
Conditions | Yield |
---|---|
With sulfuric acid at 65℃; |
(2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid
ethanol
(2R,4S)-5-([1,1'-biphenyl]-4-yl)-4-amino-2-methylpentanoic acid hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride; water In ethyl acetate at 130℃; for 1.75h; Product distribution / selectivity; |
(2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid
ethyl iodide
ethyl (2R,4S)-5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)amino)-2-methylpentanoate
Conditions | Yield |
---|---|
Stage #1: (2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid With caesium carbonate In N,N-dimethyl-formamide Stage #2: ethyl iodide In N,N-dimethyl-formamide at 20℃; Product distribution / selectivity; | |
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 16h; |
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