Lithium Hydroxide → (2S,4R)-4-Cyclopropylmethanesulfonyl-1-[5-methyl-2-(2,2,2-trifluoro-ethyl)-2H-pyrazol-3-yl]-pyrrolidine-2-carboxylic Acid

HRID 1697749Notes

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

Participants

Reactant 2

HCID 3939Lithium Hydroxide

HCID 67278701(2S,4R)-4-Cyclopropylmethanesulfonyl-1-[5-methyl-2-(2,2,2-trifluoro-ethyl)-2H-pyrazol-3-yl]-pyrrolidine-2-carboxylic Acid Methyl Ester

Product 1

HCID 66770981(2S,4R)-4-Cyclopropylmethanesulfonyl-1-[5-methyl-2-(2,2,2-trifluoro-ethyl)-2H-pyrazol-3-yl]-pyrrolidine-2-carboxylic Acid

Procedure

In analogy to the procedure described in example 253e, (2S,4R)-4-cyclopropylmethanesulfonyl-1-[5-methyl-2-(2,2,2-trifluoro-ethyl)-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=396.2 [M+H]+.

Sources & evidence

ORD record: ord-c59a50a0d2424c318f29974736c9a9d1
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163793B2

Reaction notes

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