Lithium Hydroxide → (2S,4R)-4-(4-Fluoro-2-trifluoromethyl-benzenesulfonyl)-1-[5-methyl-2-(tetrahydro-pyran-4-yl)-2H-pyrazol-3-yl]-pyrrolidine-2-carboxylic acid

HRID 1697673Notes

Reaction equation

HRID 1697673 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[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)[N:26]=[C:27]([CH3:29])[CH:28]=1)=[O:4].[OH-].[Li+]>CO>[F:19][C:16]1[CH:17]=[CH:18][C:13]([S:10]([C@H:8]2[CH2:7][N:6]([C:24]3[N:25]([CH:30]4[CH2:31][CH2:32][O:33][CH2:34][CH2:35]4)[N:26]=[C:27]([CH3:29])[CH:28]=3)[C@H:5]([C:3]([OH:4])=[O:2])[CH2:9]2)(=[O:11])=[O:12])=[C:14]([C:20]([F:22])([F:21])[F:23])[CH:15]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67278636(2S,4R)-4-(4-fluoro-2-trifluoromethyl-benzenesulfonyl)-1-[5-methyl-2-(tetrahydro-pyran-4-yl)-2H-pyrazol-3-yl]-pyrrolidine-2-carboxylic Acid Methyl Ester

Product 1

HCID 66770842(2S,4R)-4-(4-Fluoro-2-trifluoromethyl-benzenesulfonyl)-1-[5-methyl-2-(tetrahydro-pyran-4-yl)-2H-pyrazol-3-yl]-pyrrolidine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In analogy to the procedure described in example 253e, (2S,4R)-4-(4-fluoro-2-trifluoromethyl-benzenesulfonyl)-1-[5-methyl-2-(tetrahydro-pyran-4-yl)-2H-pyrazol-3-yl]-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=506.1 [M+H]+.

Sources & evidence

ORD record
ord-1fab7efa7c614b9e84c985d74833e884
Source dataset
uspto-grants-2012_04
Patent number
US08163793B2

Reaction notes

Loading…