Trifluoroacetic acid → Trifluoroacetic acid

HRID 29071Notes

Reaction equation

HRID 29071 reaction equation
C(OC(=O)[NH:7][C@@H:8]([CH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1)[C:9](=[O:28])[N:10]1[CH2:14][CH2:13][CH2:12][C@H:11]1[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:16]=1)(C)(C)C.[C:36]([OH:42])([C:38]([F:41])([F:40])[F:39])=[O:37]>C(Cl)Cl>[NH2:7][C@@H:8]([CH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1)[C:9]([N:10]1[CH2:14][CH2:13][CH2:12][C@H:11]1[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:16]=1)=[O:28].[C:36]([OH:42])([C:38]([F:41])([F:40])[F:39])=[O:37]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59787985{(S)-1-cyclohexyl-2-oxo-2-[(S)-2-(3-phenoxy-phenyl)-pyrrolidine-1-yl]-ethyl}-carbamic acid tert-butyl ester

Product 2

HCID 6422Trifluoroacetic acidHCID 59788065(S)-2-amino-2-cyclohexyl-1-[(S)-2-(3-phenoxy-phenyl)-pyrrolidin-1-yl]-ethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of {(S)-1-cyclohexyl-2-oxo-2-[(S)-2-(3-phenoxy-phenyl)-pyrrolidine-1-yl]-ethyl}-carbamic acid tert-butyl ester in CH2Cl2 (20 mL) is added TFA (10 mL) and the mixture is stirred for 30 minutes. The mixture is concentrated under reduced pressures to give (S)-2-amino-2-cyclohexyl-1-[(S)-2-(3-phenoxy-phenyl)-pyrrolidin-1-yl]-ethanone as a TFA salt quantitavely (1.65 g). LCMS m/z 379 (M+1).

Workup

  1. concentrationThe mixture is concentrated under reduced pressures

Sources & evidence

ORD record
ord-2e827d3db3754d7d9db0da6f60be045f
Source dataset
uspto-grants-2008_09
Patent number
US07419975B2

Reaction notes

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