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

Base Information

• Chemical Name: (3R,4S)-5-Cyclohexyl-2,2-difluoro-3-hydroxy-4-{(S)-2-[(S)-2-(morpholine-4-sulfonylamino)-3-phenyl-propionylamino]-3-[2-(2,2,2-trichloro-ethoxycarbonylamino)-thiazol-4-yl]-propionylamino}-pentanoic acid ethyl ester
• CAS No.: 135704-19-7
• Molecular Formula: C₃₅H₄₇Cl₃F₂N₆O₁₀S₂
• Molecular Weight: 920.28

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about (3R,4S)-5-Cyclohexyl-2,2-difluoro-3-hydroxy-4-{(S)-2-[(S)-2-(morpholine-4-sulfonylamino)-3-phenyl-propionylamino]-3-[2-(2,2,2-trichloro-ethoxycarbonylamino)-thiazol-4-yl]-propionylamino}-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: 54.0%

N-(4-MorpholinYlsulfonyl)-L-phenylalanine (124278-39-3) + (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 (142185-82-8) → (3R,4S)-5-Cyclohexyl-2,2-difluoro-3-hydroxy-4-{(S)-2-[(S)-2-(morpholine-4-sulfonylamino)-3-phenyl-propionylamino]-3-[2-(2,2,2-trichloro-ethoxycarbonylamino)-thiazol-4-yl]-propionylamino}-pentanoic acid ethyl ester (135704-19-7,142185-83-9)

Guidance literature:

With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; at 0 - 20 ℃;

DOI:10.1021/jm00092a006

Reference yield:

(S)-3-(2-Amino-thiazol-4-yl)-2-tert-butoxycarbonylamino-propionic acid benzyl ester (135704-30-2) → (3R,4S)-5-Cyclohexyl-2,2-difluoro-3-hydroxy-4-{(S)-2-[(S)-2-(morpholine-4-sulfonylamino)-3-phenyl-propionylamino]-3-[2-(2,2,2-trichloro-ethoxycarbonylamino)-thiazol-4-yl]-propionylamino}-pentanoic acid ethyl ester (135704-19-7,142185-83-9)

Guidance literature:

Multi-step reaction with 5 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

5: 54 percent / N-hydroxybenzotriazole (HOBT), dicyclohexylcarbodiimide (DCC) / dimethylformamide / 0 - 20 °C

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

DOI:10.1021/jm00092a006

Reference yield:

(S)-2-tert-Butoxycarbonylamino-3-[2-(2,2,2-trichloro-ethoxycarbonylamino)-thiazol-4-yl]-propionic acid (135703-87-6) → (3R,4S)-5-Cyclohexyl-2,2-difluoro-3-hydroxy-4-{(S)-2-[(S)-2-(morpholine-4-sulfonylamino)-3-phenyl-propionylamino]-3-[2-(2,2,2-trichloro-ethoxycarbonylamino)-thiazol-4-yl]-propionylamino}-pentanoic acid ethyl ester (135704-19-7,142185-83-9)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: 54 percent / N-hydroxybenzotriazole (HOBT), dicyclohexylcarbodiimide (DCC) / dimethylformamide / 0 - 20 °C

With hydrogenchloride; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00092a006

upstream raw materials:

N-(4-MorpholinYlsulfonyl)-L-phenylalanine

(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

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

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

Downstream raw materials:

(S)-5-Cyclohexyl-2,2-difluoro-4-{(S)-2-[(S)-2-(morpholine-4-sulfonylamino)-3-phenyl-propionylamino]-3-[2-(2,2,2-trichloro-ethoxycarbonylamino)-thiazol-4-yl]-propionylamino}-3-oxo-pentanoic acid ethyl ester

(S)-N-(4-morpholinylsulfonyl)-L-phenylalanyl-3-(2-amino-4-thiazolyl)-N-<1-(cyclohexylmethyl)-4-ethoxy-3,3-difluoro-2,4-dioxobutyl>-L-alaninamide

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