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

Base Information

• Chemical Name: tert-butyl (2S,4R)-4-([2-chloro-4-(2,2,2-trifluoroethoxy)phenyl]sulfonyl)-2-([(1-cyanocyclopropyl)amino]carbonyl)pyrrolidine-1-carboxylate
• CAS No.: 1252634-02-8
• Molecular Formula: C₂₂H₂₅ClF₃N₃O₆S
• Molecular Weight: 551.971
• Mol file: 1252634-02-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

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

C18H21ClF3NO7S + 1-amino-1-cyclopropanecarbonitrile hydrochloride (127946-77-4) → 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)

Guidance literature:

C₁₈H₂₁ClF₃NO₇S; With O-(1H-1,2,3-triazolo[4,5-b]pyridin-1-yl)-1,1,3,3-tetraethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 22 ℃; for 0.25h; Inert atmosphere;

1-amino-1-cyclopropanecarbonitrile hydrochloride; In N,N-dimethyl-formamide; for 13.5h; Inert atmosphere;

DOI:10.1002/anie.201006781

Reference yield:

1-tert-butyl 2-methyl (2S)-4-{[2-chloro-4-(2,2,2-trifluoroethoxy)phenyl]sulfonyl}pyrrolidine-1,2-dicarboxylate → 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)

Guidance literature:

Multi-step reaction with 2 steps

1.1: water; lithium hydroxide / tetrahydrofuran / 2.25 h / 22 °C

1.2: pH 3

2.1: O-(1H-1,2,3-triazolo[4,5-b]pyridin-1-yl)-1,1,3,3-tetraethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.25 h / 22 °C / Inert atmosphere

2.2: 13.5 h / Inert atmosphere

With O-(1H-1,2,3-triazolo[4,5-b]pyridin-1-yl)-1,1,3,3-tetraethyluronium hexafluorophosphate; water; N-ethyl-N,N-diisopropylamine; lithium hydroxide; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1002/anie.201006781

Reference yield: 82.0%

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)-L-prolinamide (1252634-04-0)

Guidance literature:

tert-butyl (2S,4R)-4-([2-chloro-4-(2,2,2-trifluoroethoxy)phenyl]sulfonyl)-2-([(1-cyanocyclopropyl)amino]carbonyl)pyrrolidine-1-carboxylate; With formic acid; at 22 ℃; for 6.5h;

With sodium carbonate; In water; at 0 ℃; pH=9;

DOI:10.1002/anie.201006781

upstream raw materials:

1-amino-1-cyclopropanecarbonitrile hydrochloride

Downstream raw materials:

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

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

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

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