Potassium Hydroxide → 2-[3-(2-tert-butoxycarbonylaminoethyl)-2-(3,5-dimethylphenyl)-1H-indol-5-yl]-2-methylpropionic acid
Reaction equation
[OH-].[K+].C([O:5][C:6](=[O:37])[C:7]([C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][C:14]([C:19]1[CH:24]=[C:23]([CH3:25])[CH:22]=[C:21]([CH3:26])[CH:20]=1)=[C:13]2[CH2:27][CH2:28][NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])([CH3:9])[CH3:8])C>>[C:33]([O:32][C:30]([NH:29][CH2:28][CH2:27][C:13]1[C:12]2[C:16](=[CH:17][CH:18]=[C:10]([C:7]([CH3:9])([CH3:8])[C:6]([OH:37])=[O:5])[CH:11]=2)[NH:15][C:14]=1[C:19]1[CH:24]=[C:23]([CH3:25])[CH:22]=[C:21]([CH3:26])[CH:20]=1)=[O:31])([CH3:36])([CH3:34])[CH3:35]Participants
3
Conditions
- Temperature
- 94 °C
Procedure
To a stirred solution of 2-[3-(2-tert-butoxycarbonylaminoethyl)-2-(3,5-dimethylphenyl)-1H-indol-5-yl]-2-methylpropionic acid ethyl ester (665 mg in 20 mL methanol) was added 7 mL of 2.0N potassium hydroxide and the mixture heated to 94° C. on an oil bath. After 6 hours the mixture was acidified to pH5 and extracted with ethyl acetate. The organic layer was washed with saturated ammonium chloride, dried over sodium sulfate and concentrated in vacuo to give the crude title compound (620 mg).