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

HRID 1697661Notes

Reaction equation

HRID 1697661 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]([F:19])=[CH:15][C:14]=2[C:20]([F:23])([F:22])[F:21])(=[O:12])=[O:11])[CH2:7][N:6]1[C:24]1[N:25]([CH:30]2[CH2:33][CH2:32][CH2:31]2)[N:26]=[C:27]([CH3:29])[CH:28]=1)=[O:4].[OH-].[Li+]>CO>[CH:30]1([N:25]2[C:24]([N:6]3[CH2:7][C@H:8]([S:10]([C:13]4[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=4[C:20]([F:21])([F:22])[F:23])(=[O:11])=[O:12])[CH2:9][C@H:5]3[C:3]([OH:4])=[O:2])=[CH:28][C:27]([CH3:29])=[N:26]2)[CH2:31][CH2:32][CH2:33]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 66770860(2S,4R)-1-(2-Cyclobutyl-5-methyl-2H-pyrazol-3-yl)-4-(4-fluoro-2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic Acid Methyl Ester

Product 1

HCID 66770542(2S,4R)-1-(2-Cyclobutyl-5-methyl-2H-pyrazol-3-yl)-4-(4-fluoro-2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic Acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In analogy to the procedure described in example 253e, (2S,4R)-1-(2-cyclobutyl-5-methyl-2H-pyrazol-3-yl)-4-(4-fluoro-2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic acid methyl ester was saponified in the presence of lithium hydroxide avoiding methanol as a cosolvent to give the title compound as yellow foam which was used in the next step without further purification. MS (ESI): m/z=476.2 [M+H]+.

Sources & evidence

ORD record
ord-cc82b5c87a4b49aa9f4f7936580e4240
Source dataset
uspto-grants-2012_04
Patent number
US08163793B2

Reaction notes

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