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

HRID 1697615Notes

Reaction equation

HRID 1697615 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[N:24]([CH2:29][CH:30]([CH3:32])[CH3:31])[N:25]=[C:26]([CH3:28])[CH:27]=1)=[O:4].COC([C@H]1C[C@@H](S(C2C=CC=CC=2C(F)(F)F)(=O)=O)CN1C1N(CC(C)C)N=C(C)C=1)=O.[OH-].[Li+].C(N1C(N2C[C@H](S(C3C=CC=CC=3C(F)(F)F)(=O)=O)C[C@@H]2C(O)=O)=CC(C)=N1)C(C)C>>[CH2:29]([N:24]1[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:20])([F:22])[F:21])(=[O:12])=[O:11])[CH2:9][C@H:5]2[C:3]([OH:4])=[O:2])=[CH:27][C:26]([CH3:28])=[N:25]1)[CH:30]([CH3:32])[CH3:31]

Participants

5

Reactant 4

HCID 3939Lithium HydroxideHCID 66770783(2S,4R)-1-(2-isobutyl-5-methyl-2H-pyrazol-3-yl)-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic acid methyl esterHCID 66770942(2R,4R)-1-(2-isobutyl-5-methyl-2H-pyrazol-3-yl)-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic acid methyl esterHCID 66771378(2R,4R)-1-(2-isobutyl-5-methyl-2H-pyrazol-3-yl)-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic acid

Product 1

HCID 66770813(2S,4R)-1-(2-Isobutyl-5-methyl-2H-pyrazol-3-yl)-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic Acid

Procedure

In analogy to the procedure described in example 253e, a mixture of (2S,4R)-1-(2-isobutyl-5-methyl-2H-pyrazol-3-yl)-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic acid methyl ester and (2R,4R)-1-(2-isobutyl-5-methyl-2H-pyrazol-3-yl)-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic acid methyl ester was saponified in the presence of lithium hydroxide to give a mixture of the title compound and (2R,4R)-1-(2-isobutyl-5-methyl-2H-pyrazol-3-yl)-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic acid as colorless oil which was used in the next step without further purification. MS (ESI): m/z=460.4 [M+H]+.

Workup

  1. customto give

Sources & evidence

ORD record
ord-7472385f01d448ddabe0a9bc61347a90
Source dataset
uspto-grants-2012_04
Patent number
US08163793B2

Reaction notes

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