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

HRID 1970533Notes

Reaction equation

HRID 1970533 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:26])[NH:21][CH2:22][CH:23]2[CH2:25][CH2:24]2)=[O:14])[N:8]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[N:7]=1)=[O:5])C.[OH-].[Na+]>C1COCC1.O>[CH:23]1([CH2:22][NH:21][C:20]([C@@H:16]2[CH2:17][CH2:18][CH2:19][N:15]2[C:13](=[O:14])[CH2:12][O:11][C:9]2[N:8]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[N:7]=[C:6]([C:4]([OH:5])=[O:3])[CH:10]=2)=[O:26])[CH2:24][CH2:25]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 668551565-[2-((S)-2-(Cyclopropylmethyl-carbamoyl)-pyrrolidin-1-yl)-2-oxo-ethoxy]-1-phenyl-1H-pyrazole-3-carboxylic acid ethyl ester

Product 1

HCID 668548665-[2-((S)-2-(Cyclopropylmethyl-carbamoyl)-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 1.45 g 5-[2-((S)-2-(Cyclopropylmethyl-carbamoyl)-pyrrolidin-1-yl)-2-oxo-ethoxy]-1-phenyl-1H-pyrazole-3-carboxylic acid ethyl ester in 18 ml THF and 5 ml water were added 2.3 ml aqueous NaOH (2 M) portionwise at 0° C. After 12 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: 1.50 g.

Workup

  1. filtrationfiltered
  2. washwashed with methanol

Sources & evidence

ORD record
ord-453ea0768dab49cf994ed13408853fef
Source dataset
uspto-grants-2013_04
Patent number
US08426420B2

Reaction notes

Loading…