Citric Acid → 2-Amino-3-(3-difluoromethoxy-phenyl)-propionic acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4](=[O:31])[CH:5]([N:17]=C(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH:14]([F:16])[F:15])[CH:8]=1)[CH3:2].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1>[CH2:1]([O:3][C:4](=[O:31])[CH:5]([NH2:17])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH:14]([F:16])[F:15])[CH:8]=1)[CH3:2]Participants
4
Procedure
The product from Example 175 Part A (700 mg, 1.65 mmol) was placed in a flask and dissolved in THF (30 mL). 30% (w/v) Citric acid (aqueous solution, 30 mL) was added and the reaction was stirred at rt for 72 h. The solution was extracted with diethyl ether (50 mL), and the aqueous layer was adjusted to a pH 6 using a saturated NaHCO3 solution. The aqueous solution was extracted with dichloromethane, washed with brine, dried over MgSO4, filtered and evaporated to yield 420 mg (97% yield) of a clear glass. MS 260 (M+H)+.