(3R,4S)-4-{[(S)-1-((S)-2-tert-Butoxycarbonylamino-3-methyl-butyryl)-pyrrolidine-2-carbonyl]-amino}-2,2-difluoro-3-hydroxy-5-phenyl-pentanoic acid ethyl ester

Base Information

• Chemical Name: (3R,4S)-4-{[(S)-1-((S)-2-tert-Butoxycarbonylamino-3-methyl-butyryl)-pyrrolidine-2-carbonyl]-amino}-2,2-difluoro-3-hydroxy-5-phenyl-pentanoic acid ethyl ester
• CAS No.: 191597-53-2
• Molecular Formula: C₂₈H₄₁F₂N₃O₇
• Molecular Weight: 569.646

Synonyms:

Chemical Property of (3R,4S)-4-{[(S)-1-((S)-2-tert-Butoxycarbonylamino-3-methyl-butyryl)-pyrrolidine-2-carbonyl]-amino}-2,2-difluoro-3-hydroxy-5-phenyl-pentanoic acid ethyl ester

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Technology Process of (3R,4S)-4-{[(S)-1-((S)-2-tert-Butoxycarbonylamino-3-methyl-butyryl)-pyrrolidine-2-carbonyl]-amino}-2,2-difluoro-3-hydroxy-5-phenyl-pentanoic acid ethyl ester

There total 2 articles about (3R,4S)-4-{[(S)-1-((S)-2-tert-Butoxycarbonylamino-3-methyl-butyryl)-pyrrolidine-2-carbonyl]-amino}-2,2-difluoro-3-hydroxy-5-phenyl-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:

ethyl 5-phenyl-4(S)-[(N-tert-butoxycarbonyl)amino]-2,2-difluoro-3(R)-hydroxypentanoate (103322-57-2) → (3R,4S)-4-{[(S)-1-((S)-2-tert-Butoxycarbonylamino-3-methyl-butyryl)-pyrrolidine-2-carbonyl]-amino}-2,2-difluoro-3-hydroxy-5-phenyl-pentanoic acid ethyl ester (191597-53-2)

Guidance literature:

Multi-step reaction with 2 steps

1: HCl / dioxane

2: bis(2-oxo-3-oxazolidinyl)phosphinic chloride, Et₃N

With hydrogenchloride; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine; In 1,4-dioxane;

DOI:10.1016/S0960-894X(98)00131-0

Reference yield:

N-(tert-butyloxycarbonyl)-L-valyl-L-proline (23361-28-6) + (3R,4S)-4-Amino-2,2-difluoro-3-hydroxy-5-phenyl-pentanoic acid ethyl ester (145293-59-0) → (3R,4S)-4-{[(S)-1-((S)-2-tert-Butoxycarbonylamino-3-methyl-butyryl)-pyrrolidine-2-carbonyl]-amino}-2,2-difluoro-3-hydroxy-5-phenyl-pentanoic acid ethyl ester (191597-53-2)

Guidance literature:

With bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine; Yield given;

DOI:10.1016/S0960-894X(98)00131-0

Reference yield: 100.0%

(3R,4S)-4-{[(S)-1-((S)-2-tert-Butoxycarbonylamino-3-methyl-butyryl)-pyrrolidine-2-carbonyl]-amino}-2,2-difluoro-3-hydroxy-5-phenyl-pentanoic acid ethyl ester (191597-53-2) → Sodium; (3R,4S)-4-{[(S)-1-((S)-2-tert-butoxycarbonylamino-3-methyl-butyryl)-pyrrolidine-2-carbonyl]-amino}-2,2-difluoro-3-hydroxy-5-phenyl-pentanoate

Guidance literature:

With sodium hydroxide;

DOI:10.1016/S0960-894X(98)00131-0

upstream raw materials:

N-(tert-butyloxycarbonyl)-L-valyl-L-proline

(3R,4S)-4-Amino-2,2-difluoro-3-hydroxy-5-phenyl-pentanoic acid ethyl ester

ethyl 5-phenyl-4(S)-[(N-tert-butoxycarbonyl)amino]-2,2-difluoro-3(R)-hydroxypentanoate

Downstream raw materials:

{(S)-1-[(S)-2-((1S,2R)-1-Benzyl-3,3-difluoro-2-hydroxy-3-methylcarbamoyl-propylcarbamoyl)-pyrrolidine-1-carbonyl]-2-methyl-propyl}-carbamic acid tert-butyl ester

((3R,4S)-4-{[(S)-1-((S)-2-tert-Butoxycarbonylamino-3-methyl-butyryl)-pyrrolidine-2-carbonyl]-amino}-2,2-difluoro-3-hydroxy-5-phenyl-pentanoylamino)-acetic acid methyl ester

((S)-1-{(S)-2-[(1S,2R)-1-Benzyl-3-(benzyl-methyl-carbamoyl)-3,3-difluoro-2-hydroxy-propylcarbamoyl]-pyrrolidine-1-carbonyl}-2-methyl-propyl)-carbamic acid tert-butyl ester

{(S)-1-[(S)-2-((1S,2R)-1-Benzyl-3,3-difluoro-2-hydroxy-3-phenethylcarbamoyl-propylcarbamoyl)-pyrrolidine-1-carbonyl]-2-methyl-propyl}-carbamic acid tert-butyl ester

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