Sodium Hydroxide → 5-[2-((S)-2-(2-Fluoro-ethylcarbamoyl)-pyrrolidin-1-yl)-2-oxo-ethoxy]-1-phenyl-1H-pyrazole-3-carboxylic acid

HRID 1970528Notes

Reaction equation

HRID 1970528 reaction equation
C([O:3][C:4]([C:6]1[CH:10]=[C:9]([O:11][CH2:12][C:13]([N:15]2[CH2:19][CH2:18][CH2:17][C@H:16]2[C:20](=[O:25])[NH:21][CH2:22][CH2:23][F:24])=[O:14])[N:8]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:7]=1)=[O:5])C.[OH-].[Na+]>C1COCC1.O>[F:24][CH2:23][CH2:22][NH:21][C:20]([C@@H:16]1[CH2:17][CH2:18][CH2:19][N:15]1[C:13](=[O:14])[CH2:12][O:11][C:9]1[N:8]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:7]=[C:6]([C:4]([OH:5])=[O:3])[CH:10]=1)=[O:25]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 866504755-[2-((S)-2-(2-Fluoro-ethylcarbamoyl)-pyrrolidin-1-yl)-2-oxo-ethoxy]-1-phenyl-1H-pyrazole-3-carboxylic acid ethyl ester

Product 1

HCID 866504765-[2-((S)-2-(2-Fluoro-ethylcarbamoyl)-pyrrolidin-1-yl)-2-oxo-ethoxy]-1-phenyl-1H-pyrazole-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.50 g 5-[2-((S)-2-(2-Fluoro-ethylcarbamoyl)-pyrrolidin-1-yl)-2-oxo-ethoxy]-1-phenyl-1H-pyrazole-3-carboxylic acid ethyl ester in 28 ml THF and 7 ml water were added 1.7 ml aqueous NaOH (2 M) portionwise at 0° C. After 2 h the solution was neutralized with Amberlite IR-120 ion exchange resin, filtered and washed with methanol. The crude product obtained after evaporation of the solvents was used in the subsequent reaction. Yield: 1.38 g.

Workup

  1. filtrationfiltered
  2. washwashed with methanol

Sources & evidence

ORD record
ord-7693aa8c057247f5aaa1958ecf341f02
Source dataset
uspto-grants-2013_04
Patent number
US08426420B2

Reaction notes

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