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Cas:486460-00-8
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inquiryWe are Top manufacturer for below Sitagliptin intermediates with high quality and competitive price. Boc-(R)-3-Amino-4-(2,4,5-trifluorophenyl)butanoic acid CAS:486460-00-8 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine
Cas:486460-00-8
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inquiryWhy is SINOWAY: 1) Specialized in pharmaceutical and healthcare industrial for 34 years. 2) ISO 9001:2015 & SGS audited supplier . 3) Accept various payment terms : T.T 30-60 days. 4) We have warehouse in USA with quickly shipment . 5) We c
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inquiryBoc-(R)-3-Amino-4-(2,4,5-Trifluorophenyl)Butanoic Acid[CAS:486460-00-8] Sitagliptin Butyric Acid 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine Hydrochloride[CAS:762240-92-6] HANGZHOU THINK CHEMICAL CO., LTD. (THINKC
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inquiryAs a leading manufacturer and supplier of chemicals in China, DayangChem not only supply popular chemicals, but also DayangChem's R&D center offer custom synthesis services. DayangChem can provide different quantities of custom synthesis ch
Cas:486460-00-8
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Cas:486460-00-8
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inquiryItems Standard Result Assay 98%min ----------------------------------------------------------------------------------------------
Cas:486460-00-8
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inquiryProduct Description Product website: http://www.finerchem.com/pro01en/id/220.html Product Name Boc-(R)-3-Amino-4-(2,4,5-trifluorophenyl)butanoic acid
Cas:486460-00-8
Min.Order:1 Gram
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inquiryBoc-(R)-3-Amino-4-(2,4,5-trifluorophenyl)butanoicacid Cas 486460-00-8 Company profile Wuhan Fortuna Chemical Co.,Ltd established in 2006, is a big integrative chemical enterprise being engaged in Pharmaceutical & its intermediates, Food/Feed
Cas:486460-00-8
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inquirySleeping pills and stability.This product is white or white crystalline powder;Odourless and slightly bitter taste.Almost insoluble in water, soluble in hydrochloric acid.In acid or alkali and heat hydrolysis, oral drug under the action of gastric
Cas:486460-00-8
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inquiryGood quality Good price Promptly delivery Appearance:white powder Storage:dry dondition Package:According to the demand of customer Application:intermediate Transportation:According to the demand of customer Port:shanghai
Cas:486460-00-8
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inquiryThe 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
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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
Cas:486460-00-8
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Cas:486460-00-8
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inquiryBOC-(R)-3-AMINO-4-(2,4,5-TRIFLUORO-PHENYL)-BUTYRIC ACID Basic information Product Name: BOC-(R)-3-AMINO-4-(2,4,5-TRIFLUORO-PHENYL)-BUTYRIC ACID Synonyms: BOC-(R)-3-AMINO-4-(2,4,5-TRI
Our advantages: 1. All inquiries will be replied within 12 hours. 2. Dedication to quality, supply & service. 3. Strictly on selecting raw materials. 4. Reasonable & competitive price, fast lead time. 5. Sample is available for your eva
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inquiryWITH 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
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inquiryAppearance:White powder Storage:Room temperature Package:25kg/drum Application:Sitagliptin intermediate Transportation:Express/Sea/Air Port:Any port in china
Cas:486460-00-8
Min.Order:1 Kilogram
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Type:Lab/Research institutions
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Cas:486460-00-8
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Cas:486460-00-8
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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
Cas:486460-00-8
Min.Order:1 Kilogram
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Min.Order:1 Gram
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Type:Lab/Research institutions
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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Min.Order:1 Kilogram
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inquiryProduct Detail Minimum Order Qty. 10 Gram Supply Ability 500 Kilograms/Month Storage store in cool, dry, ventilated place 20℃ Delivery Time 3 business days after payment Payment Term TT,western union,Paypal,
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Min.Order:10 Gram
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Type:Lab/Research institutions
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inquiry3-(R)-tert-butoxycarbonylamino-4-(2,4,5-trifluorophenyl)butyric acid methyl ester
(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
Conditions | Yield |
---|---|
With lithium hydroxide In tetrahydrofuran; methanol at 20℃; for 3h; | 99% |
With lithium hydroxide monohydrate; water In tetrahydrofuran for 16h; | 95.1% |
Stage #1: 3-(R)-tert-butoxycarbonylamino-4-(2,4,5-trifluorophenyl)butyric acid methyl ester With water; lithium hydroxide In methanol at 20℃; for 24h; Stage #2: With hydrogenchloride In water; ethyl acetate | 95% |
(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
Conditions | Yield |
---|---|
With palladium on carbon; hydrogen In methanol for 24h; | 99% |
(R)-tert-butyl (4-hydroxy-1-(2,4,5-trifluorophenyl)butan-2-yl)carbamate
(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
Conditions | Yield |
---|---|
With sodium hypochlorite; sodium chlorite; disodium hydrogenphosphate; sodium dihydrogenphosphate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In water; acetonitrile at 38℃; for 0.333333h; Solvent; | 98% |
With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; sodium bromide In dichloromethane at 0℃; for 2h; | 90% |
Stage #1: (R)-tert-butyl (4-hydroxy-1-(2,4,5-trifluorophenyl)butan-2-yl)carbamate With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; sodium bromide In dichloromethane at 0℃; for 2h; Stage #2: With hydrogenchloride In dichloromethane; water pH=2 - 3; | 90% |
With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical | 90% |
(R)-3-tertbutoxycarbonylamino-4-(2,4,5-trifluorophenyl)butyric acid ethyl ester
(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
Conditions | Yield |
---|---|
With lithium hydroxide monohydrate In methanol; water at 30 - 40℃; | 95% |
Stage #1: (R)-3-tertbutoxycarbonylamino-4-(2,4,5-trifluorophenyl)butyric acid ethyl ester With water; sodium hydroxide In methanol at 40 - 45℃; for 2h; Stage #2: In methanol; water pH=3; Acidic conditions; | |
Stage #1: (R)-3-tertbutoxycarbonylamino-4-(2,4,5-trifluorophenyl)butyric acid ethyl ester With sodium hydroxide In methanol; water at 40 - 45℃; for 2h; Stage #2: In methanol; water pH=3; |
[3-diazo-2-oxo-1-(2,4,5-trifluoro-benzyl)-propyl]-carbamic acid tert-butyl ester
(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
Conditions | Yield |
---|---|
With silver benzoate In 1,4-dioxane; water for 1.5h; Sonication; | 94% |
With silver benzoate In 1,4-dioxane at 20℃; for 2h; sonication; | 401 mg |
With silver benzoate In 1,4-dioxane; water for 2h; Sonographic reaction; |
(R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid
di-tert-butyl dicarbonate
(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
Conditions | Yield |
---|---|
With triethylamine In 1,4-dioxane; water at 20℃; | 91% |
Stage #1: (R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid With lithium hydroxide In 1,4-dioxane; water at 0 - 30℃; Stage #2: di-tert-butyl dicarbonate In 1,4-dioxane; water at 25 - 30℃; | 91% |
With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; for 24h; | 91% |
(R)-cyclohexyl 3-(tert-butoxycarbonyl amino)-4-(2,4,5-trifluorophenyl)butyrate
(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
Conditions | Yield |
---|---|
Stage #1: (R)-cyclohexyl 3-(tert-butoxycarbonyl amino)-4-(2,4,5-trifluorophenyl)butyrate With water; potassium carbonate at 60℃; for 3h; Stage #2: With hydrogenchloride; water at 20 - 30℃; for 2h; | 90% |
Stage #1: (R)-cyclohexyl 3-(tert-butoxycarbonyl amino)-4-(2,4,5-trifluorophenyl)butyrate With potassium carbonate In water at 60℃; for 3h; Stage #2: With hydrogenchloride In water at 20 - 30℃; for 2h; | 90% |
(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
Conditions | Yield |
---|---|
With potassium permanganate In acetone at 20℃; for 3h; Concentration; | 89% |
With ruthenium trichloride; sodium periodate In water; acetonitrile at -10℃; for 2h; | 70% |
di-tert-butyl dicarbonate
(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
Conditions | Yield |
---|---|
Stage #1: (R)-3-((R)-1-phenylethylamino)-4-(2,4,5-trifluorophenyl)-N-phenyl butanamide With 5%-palladium/activated carbon; hydrogen In methanol at 70℃; under 6000.6 Torr; Stage #2: With hydrogenchloride; water In methanol at 90℃; Stage #3: di-tert-butyl dicarbonate In tetrahydrofuran; water at 10 - 20℃; for 20h; | 88% |
di-tert-butyl dicarbonate
(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
Conditions | Yield |
---|---|
Stage #1: diethyl 2-((R)-1-((R)-1,1-dimethylethylsulfinamido)-2-(2,4,5-trifluorophenyl)ethyl)malonate With hydrogenchloride In water for 18h; Reflux; Stage #2: di-tert-butyl dicarbonate With sodium hydroxide In water at 20℃; pH=8; | 88% |
(R)-3-amino-4-(2,4,5-trifluorophenyl)butyric acid methyl ester
di-tert-butyl dicarbonate
(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
Conditions | Yield |
---|---|
Stage #1: (R)-3-amino-4-(2,4,5-trifluorophenyl)butyric acid methyl ester; di-tert-butyl dicarbonate With triethylamine In ethyl acetate at 20 - 30℃; for 7h; Stage #2: With water; sodium hydroxide In ethanol at 20 - 30℃; for 2h; | 85.5% |
Stage #1: (R)-3-amino-4-(2,4,5-trifluorophenyl)butyric acid methyl ester With water; lithium hydroxide In tetrahydrofuran at 0 - 30℃; Stage #2: di-tert-butyl dicarbonate In tetrahydrofuran; water at 25 - 30℃; for 6h; Stage #3: With sodium hydrogen sulfate In water pH=2; | 80% |
di-tert-butyl dicarbonate
(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
Conditions | Yield |
---|---|
Stage #1: di-tert-butyl 2-((R)-1-((R)-1,1-dimethylethylsulfinamido)-2-(2,4,5-trifluorophenyl)ethyl)malonate With hydrogenchloride In water for 9h; Reflux; Stage #2: di-tert-butyl dicarbonate With sodium hydroxide In water at 20℃; | 83% |
(R)-tert-butyl (1-cyano-3-(2,4,5-trifluorophenyl)propan-2-yl)carbamate
(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol at 75 - 85℃; | 81% |
With dihydrogen peroxide; sodium hydroxide In water at 100℃; for 3h; | 75% |
Stage #1: (R)-tert-butyl (1-cyano-3-(2,4,5-trifluorophenyl)propan-2-yl)carbamate With potassium hydroxide In ethanol; water at 80℃; for 12h; Stage #2: With oxalic acid In ethanol; water at 20℃; |
di-tert-butyl dicarbonate
(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
Conditions | Yield |
---|---|
Stage #1: C19H16F3NO5 With hydrogenchloride; palladium on activated charcoal; hydrogen In diethyl ether; ethanol at 20℃; for 10h; Stage #2: With hydrogenchloride In diethyl ether; ethanol for 0.5h; Reflux; Stage #3: di-tert-butyl dicarbonate With lithium hydroxide In tetrahydrofuran; diethyl ether; ethanol at 20℃; for 8h; | 66% |
di-tert-butyl dicarbonate
(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
Conditions | Yield |
---|---|
Stage #1: 2-hydroxyethyl 3-oxo-4-(2,4,5-trifluorophenyl)butanoate With pyridoxal 5'-phosphate; recombinant aminotransferase from Arthobacter sp.; water; isopropylamine In dimethyl sulfoxide at 45℃; for 24h; Green chemistry; Enzymatic reaction; Stage #2: With lithium hydroxide In dimethyl sulfoxide at 45℃; for 3h; Green chemistry; Stage #3: di-tert-butyl dicarbonate In tetrahydrofuran; dimethyl sulfoxide at 35℃; Green chemistry; enantioselective reaction; | 60.6% |
tert-butyl alcohol
(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
Conditions | Yield |
---|---|
With bromine; 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 50℃; Hofmann Rearrangement; enantioselective reaction; | 55% |
4-(2,4,5-trifluoro-phenyl)-3-oxo-butyric acid methyl ester
(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 95 percent / ammonium acetate / methanol / 7 h / Heating 2: 68 percent / H2; (R) chiral ferrocenyl derivative / chloro(1,5-cyclooctadiene)rhodium(I) dimer / 2,2,2-trifluoro-ethanol / 40 h / 50 °C / 5171.62 Torr 3: 93 percent / CH2Cl2 / 3 h / 20 °C 4: 99 percent / aq. LiOH / tetrahydrofuran; methanol / 3 h / 20 °C View Scheme | |
Multi-step reaction with 6 steps 1.1: ammonium acetate / methanol / 60 - 63 °C 2.1: sulfuric acid / methanol / -10 - 0 °C 2.2: 2 h / -10 - 0 °C 2.3: pH 8 - 9 3.1: isopropyl alcohol / 3 h / 25 - 30 °C 4.1: sodium carbonate / water / pH 8 - 9 5.1: water; lithium hydroxide / tetrahydrofuran / 0 - 30 °C 6.1: water; tetrahydrofuran / 6 h / 25 - 30 °C 6.2: pH 2 View Scheme | |
Multi-step reaction with 4 steps 1: acetic acid / methanol / Reflux; Large scale 2: boron trifluoride diethyl etherate; sodium tetrahydroborate / tetrahydrofuran / 1.5 h / -78 - 0 °C / Large scale 3: palladium 10% on activated carbon; hydrogen / methanol / 48 h / 25 °C 4: lithium hydroxide monohydrate / methanol; water / 30 - 40 °C View Scheme |
(R)-3-amino-4-(2,4,5-trifluorophenyl)butyric acid methyl ester
(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 93 percent / CH2Cl2 / 3 h / 20 °C 2: 99 percent / aq. LiOH / tetrahydrofuran; methanol / 3 h / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: water; lithium hydroxide / tetrahydrofuran / 0 - 30 °C 2.1: water; tetrahydrofuran / 6 h / 25 - 30 °C 2.2: pH 2 View Scheme |
(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 68 percent / H2; (R) chiral ferrocenyl derivative / chloro(1,5-cyclooctadiene)rhodium(I) dimer / 2,2,2-trifluoro-ethanol / 40 h / 50 °C / 5171.62 Torr 2: 93 percent / CH2Cl2 / 3 h / 20 °C 3: 99 percent / aq. LiOH / tetrahydrofuran; methanol / 3 h / 20 °C View Scheme |
(2,4,5-trifluorophenyl)acetic acid
(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 95 percent / N,N-dimethylaminopyridine; N,N-diisopropylethylamine; trimethylacetylchloride / acetonitrile / 3 h / 45 °C 2: 88.7 percent / toluene / 3 h / Heating 3: 95 percent / ammonium acetate / methanol / 7 h / Heating 4: 68 percent / H2; (R) chiral ferrocenyl derivative / chloro(1,5-cyclooctadiene)rhodium(I) dimer / 2,2,2-trifluoro-ethanol / 40 h / 50 °C / 5171.62 Torr 5: 93 percent / CH2Cl2 / 3 h / 20 °C 6: 99 percent / aq. LiOH / tetrahydrofuran; methanol / 3 h / 20 °C View Scheme | |
Multi-step reaction with 6 steps 1.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 3 h / 50 °C 2.1: ethanol / 3 h / 70 °C 3.1: formic acid / ethanol / 3 h / Reflux 3.2: 2 h / 40 °C / Reflux 4.1: methanol / Reflux 5.1: sodium carbonate / water; methanol / 3 h / 30 °C / pH 10 6.1: sodium hydroxide; water / methanol / 2 h / 40 - 45 °C 6.2: pH 3 / Acidic conditions View Scheme | |
Multi-step reaction with 8 steps 1.1: 1,1'-carbonyldiimidazole 1.2: 3 h / 50 °C 2.1: 3 h / 70 °C 3.1: ethanol / 3 h / Reflux 4.1: ethanol; sodium cyanoborohydride / 2 h / 40 °C / Reflux 5.1: methanol / Reflux 6.1: Basic conditions 7.1: sodium carbonate / water; methanol / 3 h / 30 °C / pH 10 8.1: sodium hydroxide / water; methanol / 2 h / 40 - 45 °C 8.2: pH 3 View Scheme |
5-(1-hydroxy-2-(2,4,5-trifluorophenyl)ethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione
(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 88.7 percent / toluene / 3 h / Heating 2: 95 percent / ammonium acetate / methanol / 7 h / Heating 3: 68 percent / H2; (R) chiral ferrocenyl derivative / chloro(1,5-cyclooctadiene)rhodium(I) dimer / 2,2,2-trifluoro-ethanol / 40 h / 50 °C / 5171.62 Torr 4: 93 percent / CH2Cl2 / 3 h / 20 °C 5: 99 percent / aq. LiOH / tetrahydrofuran; methanol / 3 h / 20 °C View Scheme | |
Multi-step reaction with 7 steps 1.1: 60 - 63 °C 2.1: ammonium acetate / methanol / 60 - 63 °C 3.1: sulfuric acid / methanol / -10 - 0 °C 3.2: 2 h / -10 - 0 °C 3.3: pH 8 - 9 4.1: isopropyl alcohol / 3 h / 25 - 30 °C 5.1: sodium carbonate / water / pH 8 - 9 6.1: water; lithium hydroxide / tetrahydrofuran / 0 - 30 °C 7.1: water; tetrahydrofuran / 6 h / 25 - 30 °C 7.2: pH 2 View Scheme | |
Multi-step reaction with 3 steps 1.1: acetonitrile / 24 h / 80 - 84 °C / Inert atmosphere 2.1: salicylic acid; ammonium acetate; Ru(OAc)2((R)-dm-Segphos); hydrogen / 20 h / 40 - 80 °C / Green chemistry 3.1: triethylamine / ethyl acetate / 7 h / 20 - 30 °C 3.2: 2 h / 20 - 30 °C View Scheme | |
Multi-step reaction with 7 steps 1.1: toluene / Reflux 2.1: ammonium acetate / acetonitrile / Reflux 3.1: N-tert-butylaminoborane / tetrahydrofuran / 20 °C 3.2: 8 h / 0 - 20 °C 4.1: acetonitrile; water / 0.5 h / Reflux 5.1: sodium hydrogencarbonate / water; ethyl acetate / 0.5 h 6.1: palladium on activated charcoal; hydrogen / methanol / 25 - 30 °C 7.1: sodium carbonate / tetrahydrofuran; water / 25 - 30 °C View Scheme | |
Multi-step reaction with 4 steps 1: acetonitrile / 65 °C 2: sodium tetrahydroborate; ethanol / 65 °C / Cooling with ice 3: hydrogenchloride / methanol / 20 °C / pH 1 4: sodium hydrogencarbonate / tetrahydrofuran; water / 24 h / 20 °C View Scheme |
(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: LiOH*H2O / tetrahydrofuran; H2O / 24 h 2: 14 g / LiOH*H2O / tetrahydrofuran; H2O / 12 h / 20 °C View Scheme |
di-tert-butyl dicarbonate
(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: aq. HCl / acetonitrile / 72 h / 20 °C 1.2: 2.41 g / triethylamine / CH2Cl2 / 16 h / 20 °C 2.1: aq. LiOH / tetrahydrofuran / 20 °C 3.1: isobutyl chloroformate; triethylamine / diethyl ether / 0.25 h / -20 °C 3.2: 0.36 g / diethyl ether / 1 h 4.1: 401 mg / aq. silver benzoate / dioxane / 2 h / 20 °C / sonication View Scheme |
2,4,5-trifluorobenzyl bromide
(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: n-BuLi / tetrahydrofuran / -78 °C 1.2: tetrahydrofuran / -78 °C 2.1: aq. HCl / acetonitrile / 72 h / 20 °C 2.2: 2.41 g / triethylamine / CH2Cl2 / 16 h / 20 °C 3.1: aq. LiOH / tetrahydrofuran / 20 °C 4.1: isobutyl chloroformate; triethylamine / diethyl ether / 0.25 h / -20 °C 4.2: 0.36 g / diethyl ether / 1 h 5.1: 401 mg / aq. silver benzoate / dioxane / 2 h / 20 °C / sonication View Scheme |
(R)-methyl 2-((tert-butoxycarbonyl)amino)-3-(2,4,5-trifluorophenyl)propanoate
(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: aq. LiOH / tetrahydrofuran / 20 °C 2.1: isobutyl chloroformate; triethylamine / diethyl ether / 0.25 h / -20 °C 2.2: 0.36 g / diethyl ether / 1 h 3.1: 401 mg / aq. silver benzoate / dioxane / 2 h / 20 °C / sonication View Scheme |
(2S,5R)-2,5-dihydro-3,6-dimethoxy-2-isopropyl-5-(2',4',5'-trifluorobenzyl)-pyrazine
(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: aq. HCl / acetonitrile / 72 h / 20 °C 1.2: 2.41 g / triethylamine / CH2Cl2 / 16 h / 20 °C 2.1: aq. LiOH / tetrahydrofuran / 20 °C 3.1: isobutyl chloroformate; triethylamine / diethyl ether / 0.25 h / -20 °C 3.2: 0.36 g / diethyl ether / 1 h 4.1: 401 mg / aq. silver benzoate / dioxane / 2 h / 20 °C / sonication View Scheme |
(R)-2-(tert-butoxycarbonylamino)-3-(2,4,5-trifluorophenyl)propanoic acid
(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: isobutyl chloroformate; triethylamine / diethyl ether / 0.25 h / -20 °C 1.2: 0.36 g / diethyl ether / 1 h 2.1: 401 mg / aq. silver benzoate / dioxane / 2 h / 20 °C / sonication View Scheme | |
Multi-step reaction with 2 steps 1.1: isobutyl chloroformate; triethylamine / diethyl ether / 0.25 h / -20 °C 1.2: 1 h / -20 °C 2.1: silver benzoate / water; 1,4-dioxane / 1.5 h / Sonication View Scheme | |
Multi-step reaction with 2 steps 1.1: isobutyl chloroformate; triethylamine / diethyl ether / 0.25 h / -20 °C 1.2: 1 h / -20 °C 2.1: silver benzoate / 1,4-dioxane; water / 2 h View Scheme |
di-tert-butyl dicarbonate
(R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid hydrochloride
(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
Conditions | Yield |
---|---|
With sodium carbonate In tetrahydrofuran at 0 - 20℃; |
(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
Conditions | Yield |
---|---|
Stage #1: 3-tert-butoxycarbonylamino-4-(2,4,5-trifluoro-phenyl)-butyric acid ethyl ester With water; sodium hydroxide In methanol at 40 - 45℃; Stage #2: With hydrogenchloride In water pH=2 - 3; Cooling with ice; |
(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride
(R)-tert-butyl 4-oxo-4-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-1-(2,4,5-trifluorophenyl)butan-2-ylcarbamate
Conditions | Yield |
---|---|
With 1,1'-carbonyldiimidazole In tetrahydrofuran at 55 - 60℃; for 12h; | 99.02% |
With triethylamine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride In methanol at 20 - 50℃; Reagent/catalyst; Solvent; | 96% |
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In acetonitrile at 0 - 20℃; for 24h; | 95% |
3-trifluoromethyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine
(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
(R)-tert-butyl 4-oxo-4-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-1-(2,4,5-trifluorophenyl)butan-2-ylcarbamate
Conditions | Yield |
---|---|
With (2-iodo-5-methoxyphenyl)boronic acid; 4-(dimethylamino)pyridine N-oxide In fluorobenzene for 40h; Catalytic behavior; Reagent/catalyst; | 99% |
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In water; ethyl acetate at 20℃; for 12h; | 91% |
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; for 12h; | 88% |
(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; | 98% |
(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 20h; Inert atmosphere; | 98% |
hexahydro-2-(4-cyanophenyl)-imidazo[1,5-a]pyrazin-3-one
(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
tert-butyl [(1R)-3-[2-(4-cyanophenyl)-hexahydro-3-oxoimidazo[1,5-a]pyrazin-7(8H)-yl]-3-oxo-1-(2,4,5-trifluorobenzyl)propyl]carbamate
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 12h; | 97% |
(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride
Conditions | Yield |
---|---|
Stage #1: (3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid; 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride In N,N-dimethyl-formamide for 0.166667h; Stage #2: With 2-chloro-1,3-dimethylimidazolinium chloride In N,N-dimethyl-formamide at 20 - 25℃; for 5h; Reagent/catalyst; | 97% |
(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
Conditions | Yield |
---|---|
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 0 - 30℃; for 1h; Inert atmosphere; | 97% |
(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride
sitagliptin
Conditions | Yield |
---|---|
Stage #1: (3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid With triethylamine In dichloromethane for 0.166667h; Stage #2: With benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane at 25 - 30℃; for 4h; Stage #3: 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride Further stages; | 96.5% |
hexahydro-2-(pyridin-2-yl)-imidazo[1,5-a]pyrazin-3(5h)-one
(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
tert-butyl [(1R)-3-[2-(pyridin-2-yl)-hexahydro-3-oxoimidazo[1,5-a]pyrazin-7(8H)-yl]-3-oxo-1-(2,4,5-trifluorobenzyl)propyl]carbamate
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 12h; | 96% |
(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
sitagliptin
Conditions | Yield |
---|---|
Stage #1: (3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid With thionyl chloride In ethyl acetate at 26℃; for 2h; Stage #2: 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-α]pyrazine hydrochloride With triethylamine In ethyl acetate at 25℃; Solvent; Temperature; | 96% |
Stage #1: 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-α]pyrazine hydrochloride; (3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid With 1-methyl-1H-imidazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride at 0 - 20℃; for 16h; Stage #2: With hydrogenchloride In ethanol at 20℃; for 18h; Stage #3: With sodium hydroxide In ethanol; water pH=10 - 12; Time; Solvent; | 90% |
Stage #1: (3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid With pivaloyl chloride; sodium carbonate In toluene Cooling; Stage #2: 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-α]pyrazine hydrochloride In toluene Stage #3: With hydrogenchloride In water; toluene Reagent/catalyst; | 4.4 g |
(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
(R)-3-(amino-d2)-4-(2,4,5-trifluorophenyl)-2,2-d2-butanoic acid deuterochloride
Conditions | Yield |
---|---|
With water-d2; hydrogen chloride at 70 - 160℃; for 15h; | 95% |
hexahydro-2-(3-cyanobenzyl)-imidazo[1,5-a]pyrazin-3-one
(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 12h; | 95% |
(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
(R)-tert-butyl 4-oxo-4-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-1-(2,4,5-trifluorophenyl)butan-2-ylcarbamate
Conditions | Yield |
---|---|
With pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride at 0 - 20℃; for 16h; | 95% |
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In acetonitrile at 0 - 20℃; for 24h; | 95% |
Stage #1: (3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid With Triisopropyl borate; sulfuric acid In toluene at 20℃; for 2h; Reflux; Stage #2: 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-α]pyrazine hydrochloride With triethylamine In toluene at 80℃; Reagent/catalyst; Temperature; Solvent; Concentration; Reflux; Dean-Stark; | 92.1% |
(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
Conditions | Yield |
---|---|
With 4-(dimethylamino)pyridine N-oxide; sodium hydroxide; 2,6-difluorophenylboronic acid In fluorobenzene; water at 100℃; for 23h; Reagent/catalyst; Molecular sieve; | 95% |
C14H19N3O2
(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
tert-butyl [(1R)-3-[2-(2-methoxybenzyl)-hexahydro-3-oxoimidazo[1,5-a]pyrazin-7(8H)-yl]-3-oxo-1-(2,4,5-trifluorobenzyl)propyl]carbamate
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 12h; | 94% |
4-[3-methyl-5-(trifluoromethyl)-4H-1,2,4-triazol-4-yl]piperidine
(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; | 93% |
bis(pentafluorophenyl)carbonate
(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
Conditions | Yield |
---|---|
Stage #1: (3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid With triethylamine In N,N-dimethyl-formamide at 25℃; for 0.333333h; Stage #2: bis(pentafluorophenyl)carbonate In N,N-dimethyl-formamide at 25℃; for 2h; | 92.3% |
hexahydro-2-(4-chlorobenzyl)-imidazo[1,5-a]pyrazin-3-one
(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
tert-butyl [(1R)-3-[2-(4-chlorobenzyl)-hexahydro-3-oxoimidazo[1,5-a]pyrazin-7(8H)-yl]-3-oxo-1-(2,4,5-trifluorobenzyl)propyl]carbamate
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 12h; | 92% |
7-methoxy-1,3,4,5-tetrahydrobenzo[e][1,4]diazepin-2-one hydrochloride
(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
Conditions | Yield |
---|---|
Stage #1: (3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid With N-ethyl-N,N-diisopropylamine; 1,1'-carbonyldiimidazole In acetonitrile at 20℃; for 0.5h; Stage #2: 7-methoxy-1,3,4,5-tetrahydrobenzo[e][1,4]diazepin-2-one hydrochloride In acetonitrile at 65 - 70℃; for 22h; | 92% |
bis-(p-nitrophenyl) carbonate
(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
Conditions | Yield |
---|---|
Stage #1: (3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid With triethylamine In N,N-dimethyl-formamide at 25℃; for 0.333333h; Stage #2: bis-(p-nitrophenyl) carbonate In N,N-dimethyl-formamide at 25 - 70℃; for 4h; | 91.9% |
2,2'-dipyridyl carbonate
(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
Conditions | Yield |
---|---|
Stage #1: (3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid With triethylamine In N,N-dimethyl-formamide at 25℃; for 0.333333h; Stage #2: 2,2'-dipyridyl carbonate In N,N-dimethyl-formamide at 25 - 70℃; for 2h; | 91.4% |
(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; | 91% |
(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
(R)-[3-[1,2]diazepan-1-yl-3-oxo-1-(2,4,5-trifluorobenzyl)propyl]carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 12h; | 90% |
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