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

HRID 1697757Notes

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

Participants

Reactant 2

HCID 3939Lithium Hydroxide

HCID 66770771(2S,4R)-1-(2-Cyclobutyl-5-methyl-2H-pyrazol-3-yl)-4-cyclopropylmethanesulfonyl-pyrrolidine-2-carboxylic Acid Methyl Ester

Product 1

HCID 66770974(2S,4R)-1-(2-Cyclobutyl-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-cyclobutyl-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=367.2 [M+H]+.

Sources & evidence

ORD record: ord-21c66d117f5a458b9967231fc6430caf
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163793B2

Reaction notes

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