Lithium Hydroxide → (2S,4R)-4-(2-Chloro-benzenesulfonyl)-1-[2-(4-chloro-benzyl)-5-methyl-2H-pyrazol-3-yl]-pyrrolidine-2-carboxylic Acid

HRID 1697704Notes

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

Participants

Reactant 2

HCID 3939Lithium Hydroxide

HCID 67277851(2S,4R)-4-(2-Chloro-benzenesulfonyl)-1-[2-(4-chloro-benzyl)-5-methyl-2H-pyrazol-3-yl]-pyrrolidine-2-carboxylic Acid Methyl Ester

Product 1

HCID 66770880(2S,4R)-4-(2-Chloro-benzenesulfonyl)-1-[2-(4-chloro-benzyl)-5-methyl-2H-pyrazol-3-yl]-pyrrolidine-2-carboxylic Acid

Procedure

In analogy to the procedure described in example 253e, (2S,4R)-4-(2-chloro-benzenesulfonyl)-1-[2-(4-chloro-benzyl)-5-methyl-2H-pyrazol-3-yl]-pyrrolidine-2-carboxylic acid methyl ester was saponified in the presence of lithium hydroxide to give the title compound as off-white solid which was used in the next step without further purification. MS (ESI): m/z=494.1 [M+H]+.

Sources & evidence

ORD record: ord-98fe77f6d62446bd8d3348b8b3edccab
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163793B2

Reaction notes

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