(4R)-4-{[2-chloro-4-(2,2,2-trifluoroethoxy)phenyl]sulfonyl}-N-(1-cyanocyclopropyl)-1-{[1-(5-methylthien-2-yl)cyclopropyl]carbonyl}-L-prolinamide

Base Information

• Chemical Name: (4R)-4-{[2-chloro-4-(2,2,2-trifluoroethoxy)phenyl]sulfonyl}-N-(1-cyanocyclopropyl)-1-{[1-(5-methylthien-2-yl)cyclopropyl]carbonyl}-L-prolinamide
• CAS No.: 1268445-12-0
• Molecular Formula: C₂₆H₂₅ClF₃N₃O₅S₂
• Molecular Weight: 616.082
• Mol file: 1268445-12-0.mol

Synonyms:

Chemical Property of (4R)-4-{[2-chloro-4-(2,2,2-trifluoroethoxy)phenyl]sulfonyl}-N-(1-cyanocyclopropyl)-1-{[1-(5-methylthien-2-yl)cyclopropyl]carbonyl}-L-prolinamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R)-4-{[2-chloro-4-(2,2,2-trifluoroethoxy)phenyl]sulfonyl}-N-(1-cyanocyclopropyl)-1-{[1-(5-methylthien-2-yl)cyclopropyl]carbonyl}-L-prolinamide

There total 8 articles about (4R)-4-{[2-chloro-4-(2,2,2-trifluoroethoxy)phenyl]sulfonyl}-N-(1-cyanocyclopropyl)-1-{[1-(5-methylthien-2-yl)cyclopropyl]carbonyl}-L-prolinamide 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:

(4R)-4-{[2-chloro-4-(2,2,2-trifluoroethoxy)phenyl]sulfonyl}-N-(1-cyanocyclopropyl)-L-prolinamide (1252634-04-0) + C9H9ClOS → (4R)-4-{[2-chloro-4-(2,2,2-trifluoroethoxy)phenyl]sulfonyl}-N-(1-cyanocyclopropyl)-1-{[1-(5-methylthien-2-yl)cyclopropyl]carbonyl}-L-prolinamide (1268445-12-0)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 22 ℃; for 1h; Inert atmosphere;

DOI:10.1002/anie.201006781

Reference yield:

5-methyl-2-carboxymethylthiophene (70624-30-5) → (4R)-4-{[2-chloro-4-(2,2,2-trifluoroethoxy)phenyl]sulfonyl}-N-(1-cyanocyclopropyl)-1-{[1-(5-methylthien-2-yl)cyclopropyl]carbonyl}-L-prolinamide (1268445-12-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: thionyl chloride / 0.17 h / 0 °C / Inert atmosphere

1.2: 2.33 h / 0 - 22 °C / Inert atmosphere

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 - 22 °C / Inert atmosphere

3.1: water; lithium hydroxide / tetrahydrofuran / 6 h / 22 °C

3.2: pH 3

4.1: thionyl chloride / dichloromethane / 14 h / 22 °C / Inert atmosphere

5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 22 °C / Inert atmosphere

With thionyl chloride; water; sodium hydride; N-ethyl-N,N-diisopropylamine; lithium hydroxide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; mineral oil;

DOI:10.1002/anie.201006781

Reference yield:

tert-butyl (2S,4R)-4-([2-chloro-4-(2,2,2-trifluoroethoxy)phenyl]sulfonyl)-2-([(1-cyanocyclopropyl)amino]carbonyl)pyrrolidine-1-carboxylate (1252634-02-8) → (4R)-4-{[2-chloro-4-(2,2,2-trifluoroethoxy)phenyl]sulfonyl}-N-(1-cyanocyclopropyl)-1-{[1-(5-methylthien-2-yl)cyclopropyl]carbonyl}-L-prolinamide (1268445-12-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: formic acid / 6.5 h / 22 °C

1.2: 0 °C / pH 9

2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 22 °C / Inert atmosphere

With formic acid; N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1002/anie.201006781

upstream raw materials:

5-methyl-2-carboxymethylthiophene

(4R)-4-{[2-chloro-4-(2,2,2-trifluoroethoxy)phenyl]sulfonyl}-N-(1-cyanocyclopropyl)-L-prolinamide

tert-butyl (2S,4R)-4-([2-chloro-4-(2,2,2-trifluoroethoxy)phenyl]sulfonyl)-2-([(1-cyanocyclopropyl)amino]carbonyl)pyrrolidine-1-carboxylate

1-(5-methylthien-2-yl)cyclopropanecarboxylic acid