tert-butyl (2S,4R)-4-[(2-chlorophenyl)sulfonyl]-2-{[(1-cyanocyclopropyl)amino]carbonyl}pyrrolidine-1-carboxylate

Base Information

• Chemical Name: tert-butyl (2S,4R)-4-[(2-chlorophenyl)sulfonyl]-2-{[(1-cyanocyclopropyl)amino]carbonyl}pyrrolidine-1-carboxylate
• CAS No.: 1252632-24-8
• Molecular Formula: C₂₀H₂₄ClN₃O₅S
• Molecular Weight: 453.947
• Mol file: 1252632-24-8.mol

Synonyms:tert-butyl (2S,4R)-4-[(2-chlorophenyl)sulfonyl]-2-{[(1-cyanocyclopropyl)amino]carbonyl}pyrrolidine-1-carboxylate

Chemical Property of tert-butyl (2S,4R)-4-[(2-chlorophenyl)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-chlorophenyl)sulfonyl]-2-{[(1-cyanocyclopropyl)amino]carbonyl}pyrrolidine-1-carboxylate

There total 10 articles about tert-butyl (2S,4R)-4-[(2-chlorophenyl)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: 66.0%

(2S,4R)-1-(tert-butoxycarbonyl)-4-(2-chlorophenylsulfonyl)pyrrolidine-2-carboxylic acid (1252632-16-8) + 1-amino-1-cyclopropanecarbonitrile hydrochloride (127946-77-4) → tert-butyl (2S,4R)-4-[(2-chlorophenyl)sulfonyl]-2-{[(1-cyanocyclopropyl)amino]carbonyl}pyrrolidine-1-carboxylate (1252632-24-8)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; HATU; In acetonitrile; at 20 ℃;

Reference yield:

C16H20ClNO6S + 1-amino-1-cyclopropanecarbonitrile hydrochloride (127946-77-4) → tert-butyl (2S,4R)-4-[(2-chlorophenyl)sulfonyl]-2-{[(1-cyanocyclopropyl)amino]carbonyl}pyrrolidine-1-carboxylate (1252632-24-8)

Guidance literature:

C₁₆H₂₀ClNO₆S; 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 0.416667h; Inert atmosphere;

1-amino-1-cyclopropanecarbonitrile hydrochloride; In N,N-dimethyl-formamide; for 14.5h; Inert atmosphere;

DOI:10.1002/anie.201006781

Reference yield:

1-tert-butyl 2-methyl (2S,4R)-4-[(2-chlorophenyl)sulfanyl]pyrrolidine-1,2-dicarboxylate (1252632-04-4) → tert-butyl (2S,4R)-4-[(2-chlorophenyl)sulfonyl]-2-{[(1-cyanocyclopropyl)amino]carbonyl}pyrrolidine-1-carboxylate (1252632-24-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 - 20 °C / Inert atmosphere

2: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 20 °C / Inert atmosphere

3: HATU; N-ethyl-N,N-diisopropylamine / acetonitrile / 20 °C

With lithium hydroxide monohydrate; water; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; HATU; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;

upstream raw materials:

1-amino-1-cyclopropanecarbonitrile hydrochloride

1-tert-butyl 2-methyl (2S,4R)-4-[(2-chlorophenyl)sulfanyl]pyrrolidine-1,2-dicarboxylate

(2S,4R)-1-tert-butyl 2-methyl 4-(2-chlorophenylsulfonyl)pyrrolidine-1,2-dicarboxylate

(2S,4R)-1-(tert-butoxycarbonyl)-4-(2-chlorophenylsulfonyl)pyrrolidine-2-carboxylic acid

Downstream raw materials:

(4R)-4-[(2-chlorophenyl)sulfonyl]-N-(1-cyanocyclopropyl)-1-({1-[3-(trifluoromethyl)phenyl]cyclopropyl}carbonyl)-L-prolinamide

(4R)-4-[(2-chlorophenyl)sulfonyl]-N-(1-cyanocyclopropyl)-1-{[1-(3-methoxyphenyl)cyclopropyl]carbonyl}-L-prolinamide

(4R)-1-{[1-(3-bromophenyl)cyclopropyl]carbonyl}-4-[(2-chlorophenyl)sulfonyl]-N-(1-cyanocyclopropyl)-L-prolinamide

(4R)-4-[(2-chlorophenyl)sulfonyl]-N-(1-cyanocyclopropyl)-1-(phenylacetyl)-L-prolinamide