Trifluoroacetic acid → HCID 86640344, compound

HRID 1806837Notes

Reaction equation

HRID 1806837 reaction equation
C([O:5][C:6]([CH:8]1[CH:12]([C:13]2[S:14][CH:15]=[C:16]([Br:18])[CH:17]=2)[C:11]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=2[F:28])([C:19]#[N:20])[CH:10]([CH2:29][C:30]([CH3:33])([CH3:32])[CH3:31])[NH:9]1)=[O:7])(C)(C)C.[F:34][C:35]([F:40])([F:39])[C:36]([OH:38])=[O:37]>ClCCl>[F:34][C:35]([F:40])([F:39])[C:36]([OH:38])=[O:37].[Br:18][C:16]1[CH:17]=[C:13]([CH:12]2[C:11]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=3[F:28])([C:19]#[N:20])[CH:10]([CH2:29][C:30]([CH3:31])([CH3:32])[CH3:33])[NH:9][CH:8]2[C:6]([OH:7])=[O:5])[S:14][CH:15]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67297136HCID 67297136, compound

Product 1

HCID 86640344HCID 86640344, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a manner similar to the method described in Example 25a, rac-(2R,3R,4R,5S)-3-(4-bromo-thiophen-2-yl)-4-(4-chloro-2-fluoro-phenyl)-4-cyano-5-(2,2-dimethyl-propyl)-pyrrolidine-2-carboxylic acid tert-butyl ester prepared in Example 70b (0.9 g, 1.6 mmol) was reacted with trifluoroacetic acid in dichloromethane at room temperature to give rac-(2R,3R,4R,5S)-3-(4-bromo-thiophen-2-yl)-4-(4-chloro-2-fluoro-phenyl)-4-cyano-5-(2,2-dimethyl-propyl)-pyrrolidine-2-carboxylic acid trifluoroacetic acid as a light blue solid (0.9 g, 92%).

Sources & evidence

ORD record
ord-40e09237942b4d0fbc1d8c304139c737
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

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