Trifluoroacetic acid → {5-[4-(2-Cyano-phenyl)-piperazine-1-carbonyl]-pyrrolidin-3-yl}-(benzyl)-carbamic acid 2,2,2-trichloro-ethyl ester

HRID 490578Notes

Reaction equation

HRID 490578 reaction equation
C(OC([N:8]1[CH2:12][CH:11]([N:13]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:14]([O:16][CH2:17][C:18]([Cl:21])([Cl:20])[Cl:19])=[O:15])[CH2:10][CH:9]1[C:29]([N:31]1[CH2:36][CH2:35][N:34]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=2[C:43]#[N:44])[CH2:33][CH2:32]1)=[O:30])=O)(C)(C)C.C(O)(C(F)(F)F)=O>>[Cl:21][C:18]([Cl:19])([Cl:20])[CH2:17][O:16][C:14](=[O:15])[N:13]([CH:11]1[CH2:10][CH:9]([C:29]([N:31]2[CH2:32][CH2:33][N:34]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=3[C:43]#[N:44])[CH2:35][CH2:36]2)=[O:30])[NH:8][CH2:12]1)[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 675465492-[4-(2-Cyano-phenyl)-piperazine-1-carbonyl]-4-[(benzyl)-(2,2,2-trichloroethoxycarbonyl)-amino]-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 67547167{5-[4-(2-Cyano-phenyl)-piperazine-1-carbonyl]-pyrrolidin-3-yl}-(benzyl)-carbamic acid 2,2,2-trichloro-ethyl ester

Procedure

A mixture of 2-[4-(2-cyano-phenyl)-piperazine-1-carbonyl]-4-[(benzyl)-(2,2,2-trichloroethoxycarbonyl)-amino]-pyrrolidine-1-carboxylic acid tert-butyl ester and CF3COOH are stirred at rt for about 5 h, and then concentrated to give {5-[4-(2-cyano-phenyl)-piperazine-1-carbonyl]-pyrrolidin-3-yl}-(benzyl)-carbamic acid 2,2,2-trichloro-ethyl ester (22).

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-9051a48db60844f48442177a54b85633
Source dataset
uspto-grants-2009_05
Patent number
US07528136B2

Reaction notes

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