Potassium Hydroxide → HCID 67135277, compound

HRID 536036Notes

Reaction equation

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

Participants

Conditions

Temperature: 52.5 °C

Procedure

1-[1-(2,4-Difluoro-phenyl)-5-oxo-pyrrolidin-3-ylmethyl]-1H-pyrazole-4-carboxylic acid ethyl ester (0.222 g, 0.62 mmol) was dissolved in a mixture of solvents Methanol:water (3:1, 5 ml) and KOH (0.07 g, 125 mmol) was added to the reaction mixture and then stirred at 50-55° C. for 3 hours. Solvents were removed and the residue was diluted with water (3 ml) and washed with DCM (3×10 ml) and acidified with dil. HCl. It was extracted with ethyl acetate (3×15 ml), organic layers were mixed and washed with brine (20 ml), dried over Na2SO4 and evaporated to dryness to obtain 1-[1-(2,4-Difluoro-phenyl)-5-oxo-pyrrolidin-3-ylmethyl]-1H-pyrazole-4-carboxylic acid (0.18 g, 90%) as a brownish sticky mass.

Workup

additionwas added to the reaction mixture
customSolvents were removed
additionthe residue was diluted with water (3 ml)
washwashed with DCM (3×10 ml)
extractionIt was extracted with ethyl acetate (3×15 ml), organic layers
additionwere mixed
washwashed with brine (20 ml)
dry with materialdried over Na2SO4
customevaporated to dryness

Sources & evidence

ORD record: ord-f1d650d05fcb4d33afc24444db356047
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859566B2

Reaction notes

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