Sodium Hydroxide → 3-[(2-Phenyl-5-trifluoromethyloxazole-4-carbonyl)amino]propionic acid

HRID 632934Notes

Reaction equation

HRID 632934 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:26])[CH2:6][CH2:7][NH:8][C:9]([C:11]1[N:12]=[C:13]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[O:14][C:15]=1[C:16]([F:19])([F:18])[F:17])=[O:10]>C1COCC1.CO.O>[C:20]1([C:13]2[O:14][C:15]([C:16]([F:19])([F:18])[F:17])=[C:11]([C:9]([NH:8][CH2:7][CH2:6][C:5]([OH:26])=[O:4])=[O:10])[N:12]=2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 1179200823-[(2-Phenyl-5-trifluoromethyloxazole-4-carbonyl)amino]propionic acid methyl ester

Product 1

HCID 1179201883-[(2-Phenyl-5-trifluoromethyloxazole-4-carbonyl)amino]propionic acidYield 98.9%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Conditions

Temperature
25 °C

Procedure

NaOH (309.7 mg, 7.7 mmol) was added to 3-[(2-phenyl-5-trifluoromethyloxazole-4-carbonyl)amino]propionic acid methyl ester (265 mg, 0.77 mmol) dissolved in THF/MeOH/water (25 mL, 4:2:1). The reaction mixture was stirred at 25° C. for 12 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 (250 mg, 98%) as a white solid.

Workup

  1. concentrationconcentrated under vacuum
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried with anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-54486846bd7e4281a3db52f65d60ffcb
Source dataset
uspto-grants-2016_04
Patent number
US09321728B2

Reaction notes

Loading…