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

HRID 1697782Notes

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

Participants

Reactant 2

HCID 3939Lithium Hydroxide

HCID 67278217(2S,4R)-4-(2-Chloro-benzenesulfonyl)-1-(3-chloro-[1,2,4]thiadiazol-5-yl)-pyrrolidine-2-carboxylic Acid Methyl Ester

Product 1

HCID 66771355(2S,4R)-4-(2-Chloro-benzenesulfonyl)-1-(3-chloro-[1,2,4]thiadiazol-5-yl)-pyrrolidine-2-carboxylic Acid

Procedure

In analogy to the procedure described in example 253e, (2S,4R)-4-(2-chloro-benzenesulfonyl)-1-(3-chloro-[1,2,4]thiadiazol-5-yl)-pyrrolidine-2-carboxylic acid methyl ester was saponified in the presence of lithium hydroxide to give the title compound as yellow oil which was used in the next step without further purification. MS (ESI): m/z=406.0 [M−H]−.

Sources & evidence

ORD record: ord-ea36ba92c0ed4ef9a3762c31a2fca979
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163793B2

Reaction notes

Loading…