Lithium Hydroxide → (2S,4R)-1-(1,5-Dimethyl-1H-pyrazol-3-yl)-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic Acid

HRID 1697564Notes

Reaction equation

C[O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]([F:22])([F:21])[F:20])(=[O:12])=[O:11])[CH2:7][N:6]1[C:23]1[CH:27]=[C:26]([CH3:28])[N:25]([CH3:29])[N:24]=1)=[O:4].[OH-].[Li+]>>[CH3:29][N:25]1[C:26]([CH3:28])=[CH:27][C:23]([N:6]2[CH2:7][C@H:8]([S:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:19]([F:21])([F:22])[F:20])(=[O:11])=[O:12])[CH2:9][C@H:5]2[C:3]([OH:4])=[O:2])=[N:24]1

Participants

Reactant 2

HCID 3939Lithium Hydroxide

HCID 66771910(2S,4R)-1-(1,5-Dimethyl-1H-pyrazol-3-yl)-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic Acid Methyl Ester

Product 1

HCID 66772098(2S,4R)-1-(1,5-Dimethyl-1H-pyrazol-3-yl)-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic Acid

Procedure

In analogy to the procedure described in example 253e, (2S,4R)-1-(1,5-dimethyl-1H-pyrazol-3-yl)-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic acid methyl ester was saponified in the presence of lithium hydroxide to give the title compound as off-white solid. MS (ESI): m/z=418.2 [M+H]+.

Sources & evidence

ORD record: ord-d98b11ea528c43bd87920d8b2c19fdf6
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163793B2

Reaction notes

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