(3R,4S)-4-{(S)-2-Amino-3-[2-(2,2,2-trichloro-ethoxycarbonylamino)-thiazol-4-yl]-propionylamino}-5-cyclohexyl-2,2-difluoro-3-hydroxy-pentanoic acid ethyl ester

Base Information

Chemical Name:(3R,4S)-4-{(S)-2-Amino-3-[2-(2,2,2-trichloro-ethoxycarbonylamino)-thiazol-4-yl]-propionylamino}-5-cyclohexyl-2,2-difluoro-3-hydroxy-pentanoic acid ethyl ester
CAS No.:142185-82-8
Molecular Formula:C₂₂H₃₁Cl₃F₂N₄O₆S
Molecular Weight:623.933
Hs Code.:

(3R,4S)-4-{(S)-2-Amino-3-[2-(2,2,2-trichloro-ethoxycarbonylamino)-thiazol-4-yl]-propionylamino}-5-cyclohexyl-2,2-difluoro-3-hydroxy-pentanoic acid ethyl ester

Synonyms:(3R,4S)-4-{(S)-2-Amino-3-[2-(2,2,2-trichloro-ethoxycarbonylamino)-thiazol-4-yl]-propionylamino}-5-cyclohexyl-2,2-difluoro-3-hydroxy-pentanoic acid ethyl ester

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Chemical Property of (3R,4S)-4-{(S)-2-Amino-3-[2-(2,2,2-trichloro-ethoxycarbonylamino)-thiazol-4-yl]-propionylamino}-5-cyclohexyl-2,2-difluoro-3-hydroxy-pentanoic acid ethyl ester

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Technology Process of (3R,4S)-4-{(S)-2-Amino-3-[2-(2,2,2-trichloro-ethoxycarbonylamino)-thiazol-4-yl]-propionylamino}-5-cyclohexyl-2,2-difluoro-3-hydroxy-pentanoic acid ethyl ester

There total 5 articles about (3R,4S)-4-{(S)-2-Amino-3-[2-(2,2,2-trichloro-ethoxycarbonylamino)-thiazol-4-yl]-propionylamino}-5-cyclohexyl-2,2-difluoro-3-hydroxy-pentanoic acid ethyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

: 142185-81-7
(3R,4S)-4-{(S)-2-tert-Butoxycarbonylamino-3-[2-(2,2,2-trichloro-ethoxycarbonylamino)-thiazol-4-yl]-propionylamino}-5-cyclohexyl-2,2-difluoro-3-hydroxy-pentanoic acid ethyl ester

: 142185-82-8
(3R,4S)-4-{(S)-2-Amino-3-[2-(2,2,2-trichloro-ethoxycarbonylamino)-thiazol-4-yl]-propionylamino}-5-cyclohexyl-2,2-difluoro-3-hydroxy-pentanoic acid ethyl ester

Guidance literature:: With hydrogenchloride; In methanol; dichloromethane; Ambient temperature;
DOI:10.1021/jm00092a006

Reference yield:

: 135704-30-2
(S)-3-(2-Amino-thiazol-4-yl)-2-tert-butoxycarbonylamino-propionic acid benzyl ester

: 142185-82-8
(3R,4S)-4-{(S)-2-Amino-3-[2-(2,2,2-trichloro-ethoxycarbonylamino)-thiazol-4-yl]-propionylamino}-5-cyclohexyl-2,2-difluoro-3-hydroxy-pentanoic acid ethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 98 percent / DMAP / CH₂Cl₂ / 4 h / -20 °C

2: 84 percent / aq. KOH / methanol / 3.5 h / Ambient temperature

3: 28 percent / N-hydroxybenzotriazole (HOBT), dicyclohexylcarbodiimide (DCC), Et₃N / dimethylformamide / 0 - 20 °C

4: 91 percent / HCl (gas) / CH₂Cl₂; methanol / Ambient temperature

With hydrogenchloride; dmap; potassium hydroxide; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm00092a006

Reference yield:

: 135703-87-6
(S)-2-tert-Butoxycarbonylamino-3-[2-(2,2,2-trichloro-ethoxycarbonylamino)-thiazol-4-yl]-propionic acid

: 142185-82-8
(3R,4S)-4-{(S)-2-Amino-3-[2-(2,2,2-trichloro-ethoxycarbonylamino)-thiazol-4-yl]-propionylamino}-5-cyclohexyl-2,2-difluoro-3-hydroxy-pentanoic acid ethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 28 percent / N-hydroxybenzotriazole (HOBT), dicyclohexylcarbodiimide (DCC), Et₃N / dimethylformamide / 0 - 20 °C

2: 91 percent / HCl (gas) / CH₂Cl₂; methanol / Ambient temperature

With hydrogenchloride; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm00092a006