(R)-4-ethyl-1-[4-(trifluoromethyl)phenyl]-2-azetidinone → methyl (3R)-3-(4-trifluoromethylphenylamino)-pentanoate
Reaction equation
[CH2:1]([C@H:3]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=2)C(=O)[CH2:4]1)[CH3:2].[CH3:18][O-:19].[Na+].[CH3:21][OH:22]>CO>[F:14][C:13]([F:15])([F:16])[C:10]1[CH:9]=[CH:8][C:7]([NH:6][C@H:3]([CH2:1][CH3:2])[CH2:4][C:18]([O:22][CH3:21])=[O:19])=[CH:12][CH:11]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
420 mg (1.73 mmol) of (R)-4-ethyl-1-[4-(trifluoromethyl)phenyl]-2-azetidinone produced in Example 6 was dissolved in methanol (7.0 mL) and further mixed with 668 mg (3.46 mmol) of 28 wt % sodium methoxide/methanol solution at room temperature. After stirring at the same temperature for further 1 hour, the solvent was removed by distillation under reduced pressure and 1 N hydrochloric acid (5.0 mL) was added and extraction with ethyl acetate was carried out. The organic layer was washed with an aqueous saturated sodium hydrogen carbonate solution, and the product was dried with anhydrous magnesium sulfate and concentrated under reduced pressure to obtain methyl (R)-3-[4-(trifluoromethyl)phenylamino]-pentanoate as a colorless oil (459 mg, crude yield: 97%).