Lithium Hydroxide → (2S,4R)-4-(2-Chloro-4-fluoro-benzenesulfonyl)-1-(2-cyclobutyl-5-methyl-2H-pyrazol-3-yl)-pyrrolidine-2-carboxylic Acid

HRID 1697655Notes

Reaction equation

HRID 1697655 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][C:16]([F:19])=[CH:15][C:14]=2[Cl:20])(=[O:12])=[O:11])[CH2:7][N:6]1[C:21]1[N:22]([CH:27]2[CH2:30][CH2:29][CH2:28]2)[N:23]=[C:24]([CH3:26])[CH:25]=1)=[O:4].[OH-].[Li+]>CO>[Cl:20][C:14]1[CH:15]=[C:16]([F:19])[CH:17]=[CH:18][C:13]=1[S:10]([C@H:8]1[CH2:7][N:6]([C:21]2[N:22]([CH:27]3[CH2:30][CH2:29][CH2:28]3)[N:23]=[C:24]([CH3:26])[CH:25]=2)[C@H:5]([C:3]([OH:4])=[O:2])[CH2:9]1)(=[O:12])=[O:11]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67278407(2S,4R)-4-(2-Chloro-4-fluoro-benzenesulfonyl)-1-(2-cyclobutyl-5-methyl-2H-pyrazol-3-yl)-pyrrolidine-2-carboxylic Acid Methyl Ester

Product 1

HCID 66770457(2S,4R)-4-(2-Chloro-4-fluoro-benzenesulfonyl)-1-(2-cyclobutyl-5-methyl-2H-pyrazol-3-yl)-pyrrolidine-2-carboxylic Acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In analogy to the procedure described in example 253e, (2S,4R)-4-(2-chloro-4-fluoro-benzenesulfonyl)-1-(2-cyclobutyl-5-methyl-2H-pyrazol-3-yl)-pyrrolidine-2-carboxylic acid methyl ester (example 375c) was saponified in the presence of lithium hydroxide avoiding methanol as a cosolvent to give the title compound as yellow oil which was used in the next step without further purification. MS (ESI): m/z=442.2 [M+H]+.

Sources & evidence

ORD record
ord-e74a44f7daf74945b1f1b8c46afc3971
Source dataset
uspto-grants-2012_04
Patent number
US08163793B2

Reaction notes

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