Sodium Hydroxide → 3-[(1-phenyl-3-trifluoromethyl-1H-pyrazole-4-carbonyl)amino]propionic acid

HRID 632937Notes

Reaction equation

[OH-].[Na+].C[O:4][C:5](=[O:26])[CH2:6][CH2:7][NH:8][C:9]([C:11]1[C:12]([C:22]([F:25])([F:24])[F:23])=[N:13][N:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:15]=1)=[O:10]>C1COCC1.CO.O>[C:16]1([N:14]2[CH:15]=[C:11]([C:9]([NH:8][CH2:7][CH2:6][C:5]([OH:26])=[O:4])=[O:10])[C:12]([C:22]([F:24])([F:25])[F:23])=[N:13]2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

Conditions

Temperature: 25 °C

Procedure

NaOH (212.1 mg, 5.3 mmol) was added to 3-[(1-phenyl-3-trifluoromethyl-1H-pyrazole-4-carbonyl)amino]propionic acid methyl ester (181 mg, 0.53 mmol) dissolved in THF/MeOH/water (25 mL, 4:2:1). The reaction mixture was stirred at 25° C. for 5 hours and concentrated under vacuum. The residue was acidified with 1M HCl up to pH 2 and extracted with ethyl acetate. The extract was washed with brine and dried with anhydrous sodium sulfate and concentrated under vacuum to obtain the desired compound (170 mg, 98%) as a white solid.

Workup

concentrationconcentrated under vacuum
extractionextracted with ethyl acetate
washThe extract was washed with brine
dry with materialdried with anhydrous sodium sulfate
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-b4461aacc87b44198728c08657ddfb96
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321728B2

Reaction notes

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