Lithium Hydroxide → (2S,4R)-1-(2-Isopropyl-5-methyl-2H-pyrazol-3-yl)-4-[4-(2,2,2-trifluoro-ethoxy)-2-trifluoromethyl-benzenesulfonyl]-pyrrolidine-2-carboxylic Acid

HRID 1697598Notes

Reaction equation

HRID 1697598 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][C:16]([O:19][CH2:20][C:21]([F:24])([F:23])[F:22])=[CH:15][C:14]=2[C:25]([F:28])([F:27])[F:26])(=[O:12])=[O:11])[CH2:7][N:6]1[C:29]1[N:30]([CH:35]([CH3:37])[CH3:36])[N:31]=[C:32]([CH3:34])[CH:33]=1)=[O:4].COC([C@H]1C[C@@H](S(C2C=CC(OCC(F)(F)F)=CC=2C(F)(F)F)(=O)=O)CN1C1N(C(C)C)N=C(C)C=1)=O.[OH-].[Li+]>>[CH:35]([N:30]1[C:29]([N:6]2[CH2:7][C@H:8]([S:10]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]([F:22])([F:23])[F:24])=[CH:15][C:14]=3[C:25]([F:28])([F:27])[F:26])(=[O:12])=[O:11])[CH2:9][C@H:5]2[C:3]([OH:4])=[O:2])=[CH:33][C:32]([CH3:34])=[N:31]1)([CH3:37])[CH3:36]

Participants

4

Reactant 3

HCID 3939Lithium HydroxideHCID 86646839(2S,4R)-1-(2-Isopropyl-5-methyl-2H-pyrazol-3-yl)-4-[4-(2,2,2-trifluoro-ethoxy)-2-trifluoromethyl-benzenesulfonyl]-pyrrolidine-2-carboxylic Acid Methyl EsterHCID 86646842(2R,4R)-1-(2-isopropyl-5-methyl-2H-pyrazol-3-yl)-4-[4-(2,2,2-trifluoro-ethoxy)-2-trifluoromethyl-benzenesulfonyl]-pyrrolidine-2-carboxylic acid methyl ester

Product 1

HCID 86646841(2S,4R)-1-(2-Isopropyl-5-methyl-2H-pyrazol-3-yl)-4-[4-(2,2,2-trifluoro-ethoxy)-2-trifluoromethyl-benzenesulfonyl]-pyrrolidine-2-carboxylic Acid

Procedure

In analogy to the procedure described in example 253e, a mixture of (2S,4R)-1-(2-isopropyl-5-methyl-2H-pyrazol-3-yl)-4-[4-(2,2,2-trifluoro-ethoxy)-2-trifluoromethyl-benzenesulfonyl]-pyrrolidine-2-carboxylic acid methyl ester and (2R,4R)-1-(2-isopropyl-5-methyl-2H-pyrazol-3-yl)-4-[4-(2,2,2-trifluoro-ethoxy)-2-trifluoromethyl-benzenesulfonyl]-pyrrolidine-2-carboxylic acid methyl ester was saponified in the presence of lithium hydroxide to give the title compound as colorless solid. MS (ESI): m/z=544.2 [M+H]+.

Sources & evidence

ORD record
ord-edacd0132a9749c6b0878633f6bfc1d9
Source dataset
uspto-grants-2012_04
Patent number
US08163793B2

Reaction notes

Loading…