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

HRID 1697717Notes

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

Participants

Reactant 2

HCID 3939Lithium Hydroxide

HCID 66771360(2S,4R)-1-(2-benzyl-5-methyl-2H-pyrazol-3-yl)-4-cyclopropylmethanesulfonyl-pyrrolidine-2-carboxylic Acid Methyl Ester

Product 1

HCID 66770493(2S,4R)-1-(2-Benzyl-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-benzyl-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=404.2 [M+H]+.

Sources & evidence

ORD record: ord-eb9670c81c224e0bbe7750f77b8b37de
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163793B2

Reaction notes

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