Lithium Hydroxide → (2S)-2-[(1,2,3,3a,4,8b-Hexahydrocyclopenta[b]Indol-5-ylcarbonyl)Amino]-Propanoic Acid
Reaction equation
[OH-].[Li+].[CH2:3]1[CH:14]2[CH:6]([NH:7][C:8]3[C:9]([C:15]([NH:17][C@@H:18]([CH3:24])[C:19]([O:21]CC)=[O:20])=[O:16])=[CH:10][CH:11]=[CH:12][C:13]=32)[CH2:5][CH2:4]1>C1COCC1>[CH2:3]1[CH:14]2[CH:6]([NH:7][C:8]3[C:9]([C:15]([NH:17][C@@H:18]([CH3:24])[C:19]([OH:21])=[O:20])=[O:16])=[CH:10][CH:11]=[CH:12][C:13]=32)[CH2:5][CH2:4]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A 1 M aqueous lithium hydroxide solution (13 mmol, 13 mL) was added to a solution of ethyl (2S)-2-[(1,2,3,3a,4,8b-hexahydrocyclopenta[b]indol-5-ylcarbonyl)amino]propanoate (6.1 mmol, 1.9 g) in THF (50 mL). The reaction mixture was stirred at room temperature for 18 h. The reaction was concentrated in vacuo and diluted with 0.1 N HCl and ethyl acetate. The phases were separated and the organic phase was washed with water, dried over MgSO4, filtered, and concentrated to give a yellow oil (1.6 g, 6.1 mmol, quantitative yield).