Lithium Hydroxide → (2S,4R)-1-(3-Chloro-[1,2,4]thiadiazol-5-yl)-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic Acid

HRID 1697690Notes

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

Participants

Reactant 2

HCID 3939Lithium Hydroxide

HCID 66772233(2S,4R)-1-(3-Chloro-[1,2,4]thiadiazol-5-yl)-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic Acid Methyl Ester

Product 1

HCID 66771345(2S,4R)-1-(3-Chloro-[1,2,4]thiadiazol-5-yl)-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic Acid

Procedure

In analogy to the procedure described in example 253e, (2S,4R)-1-(3-chloro-[1,2,4]thiadiazol-5-yl)-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic acid methyl ester was saponified in the presence of lithium hydroxide to give the title compound as brown solid. MS (ESI): m/z=442.1 [M+H]+.

Sources & evidence

ORD record: ord-ae3628257cbb433095130bc926418aba
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163793B2

Reaction notes

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