Lithium Hydroxide → (2S,4R)-4-(2-Chloro-4-fluorophenylsulfonyl)-1-(3-methyl-1-phenethyl-1H-pyrazol-5-yl)pyrrolidine-2-carboxylic Acid

HRID 1697777Notes

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

Participants

Reactant 2

HCID 3939Lithium Hydroxide

HCID 66772109(2S,4R)-4-(2-Chloro-4-fluorophenylsulfonyl)-1-(3-methyl-1-phenethyl-1H-pyrazol-5-yl)pyrrolidine-2-carboxylic Acid Methyl Ester

Product 1

HCID 66771951(2S,4R)-4-(2-Chloro-4-fluorophenylsulfonyl)-1-(3-methyl-1-phenethyl-1H-pyrazol-5-yl)pyrrolidine-2-carboxylic Acid

Procedure

In analogy to the procedure described in example 253e, (2S,4R)-4-(2-chloro-4-fluorophenylsulfonyl)-1-(3-methyl-1-phenethyl-1H-pyrazol-5-yl)pyrrolidine-2-carboxylic acid methyl ester was saponified in the presence of lithium hydroxide to give the title compound as yellow foam which was used in the next step without further purification. MS (ESI): m/z=492.1 [M+H]+.

Sources & evidence

ORD record: ord-d72227265e3b448b9e9c5e27bb4e1077
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163793B2

Reaction notes

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