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

HRID 1697751Notes

Reaction equation

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

Participants

Reactant 2

HCID 3939Lithium Hydroxide

HCID 86646871(2S,4R)-1-[2-(2-Chloro-pyridin-4-yl)-5-methyl-2H-pyrazol-3-yl]-4-cyclopropylmethanesulfonyl-pyrrolidine-2-carboxylic Acid Methyl Ester

Product 1

HCID 86646872(2S,4R)-1-[2-(2-Chloro-pyridin-4-yl)-5-methyl-2H-pyrazol-3-yl]-4-cyclopropylmethanesulfonyl-pyrrolidine-2-carboxylic Acid

Procedure

In analogy to the procedure described in example 253e, (2S,4R)-1-[2-(2-chloro-pyridin-4-yl)-5-methyl-2H-pyrazol-3-yl]-4-cyclopropylmethanesulfonyl-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=425.0 [M+H]+.

Sources & evidence

ORD record: ord-eb5b3fe5bb164e29b22da45c1d669a8b
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163793B2

Reaction notes

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