Lithium Hydroxide → (1-Oxo-1,2,3,10-tetrahydro-azepino[3,4-b]indol-5-yl)-acetic acid
Reaction equation
C(OC([N:8]1[CH2:21][CH2:20][C:19](=[CH:22][C:23]([O:25]CC)=[O:24])[C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11](C(OC(C)(C)C)=O)[C:10]=2[C:9]1=[O:35])=O)(C)(C)C.[Li+].[OH-]>CO.O>[O:35]=[C:9]1[C:10]2[NH:11][C:12]3[C:17]([C:18]=2[C:19]([CH2:22][C:23]([OH:25])=[O:24])=[CH:20][CH2:21][NH:8]1)=[CH:16][CH:15]=[CH:14][CH:13]=3Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 5-ethoxycarbonylmethylene-1-oxo-1,3,4,5-tetrahydro-azepino[3,4-b]indole-2,10-dicarboxylic acid di-tert-butyl ester, (0.496 g, 1.02 mmol) and LiOH (0.246 g, 10.2 mmol) in MeOH—H2O (1:1 mixture, 50 mL) is stirred at room temperature for 2 days before it is concentrated. Water is added to the residue and it is acidified with NaHSO4 (2M). The solid that is precipitated is collected by vacuum filtration and dried to yield (1-oxo-1,2,3,10-tetrahydro-azepino[3,4-b]indol-5-yl)-acetic acid; 1H NMR (DMSO-d6) δ 2.50 (t, 2H, J=5.6 Hz), 2.82 (s, 1H), 5.00 (t, 1H, J=6.4 Hz), 6.18 (t, 1H, J=7.2 Hz), 6.34 (t, 1H, J=7.2 Hz), 6.56 (d, 1H, J=8.8 Hz), 6.90 (d, 1H, J=8.8 Hz), 7.21 (t, 1H, J=4.4 Hz), 10.98 (s, 1H); m/z [M++1] 257.0.