Trifluoroacetic acid → HCID 67546447, compound

HRID 490625Notes

Reaction equation

HRID 490625 reaction equation
C(OC([N:8]1[CH2:12][CH:11]([N:13]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=2[F:30])[C:14]([O:16][CH2:17][C:18]([Cl:21])([Cl:20])[Cl:19])=[O:15])[CH2:10][CH:9]1[C:31]([N:33]1[CH2:38][CH2:37][N:36]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=2[C:45]#[N:46])[CH2:35][CH2:34]1)=[O:32])=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:31]([N:33]2[CH2:38][CH2:37][N:36]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=3[C:45]#[N:46])[CH2:35][CH2:34]2)=[O:32])[NH:8][CH2:12]1)[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=1[F:30]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67546806HCID 67546806, compound

Product 1

HCID 67546447HCID 67546447, compoundYield 90.6%

Procedure

A mixture of 2-[4-(2-cyano-phenyl)-piperazine-1-carbonyl]-4-[(2,4-difluoro-benzyl)-(2,2,2-trichloroethoxycarbonyl)-amino]-pyrrolidine-1-carboxylic acid tert-butyl ester (4.5 g, 6.4 mmol) and CF3COOH (3.65 g, 32 mmol) were stirred at rt. for 5 h, and then concentrated to give the crude product as dark yellow oil (3.5 g, 5.8 mmol).

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-888769186e2f430cb9c53f16fb852180
Source dataset
uspto-grants-2009_05
Patent number
US07528136B2

Reaction notes

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