Ethyl Acetate → HCID 19608775, compound
Reaction equation
[CH3:1][O:2][C:3]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[C:9]([C:14]([OH:16])=O)[CH:8]=2)=[O:4].Cl.[C:18]([O:22][C:23](=[O:26])[CH2:24][NH2:25])([CH3:21])(C)C.C([O-])(O)=O.[Na+].[CH3:32][CH2:33]OC(C)=O>>[CH2:18]([O:22][C:23]([CH2:24][NH:25][C:14]([C:9]1[CH:8]=[C:7]2[C:12]([CH:13]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[NH:6]2)=[CH:11][CH:10]=1)=[O:16])=[O:26])[CH2:21][CH2:32][CH3:33]Participants
Procedure
2-(Methoxycarbonyl)indole-6-carboxylic acid was coupled with glycine t-butyl ester hydrochloride in the presence of NaHCO3 (1 equivalent) by the method described above to give N-[(butoxycarbonyl)methyl]-2-(methoxycarbonyl)indole-6-carboxamide as a white solid (86%), mp 181-183.5° C. (EtOAc). 1H NMR (CDCl3) δ9.58 (s, 1H, indole NH), 8.06 (s, 1H, H-3 or H-7), 7.68 (d, J=8.4 Hz, 1H, H-4), 7.52 (dd, J=8.4, 1.5 Hz, 1H, H-5), 7.20 (dd, J=2.0, 0.8 Hz, 1H, H-3 or H-7), 6.82 (t, J=4.7 Hz, 1H, amide NH), 4.20 (d, J=5.0 Hz, 2H, CH2), 3.96 (s, 3H, CO2Me), 1.51 (s, 9H, t-Bu); 13C NMR δ169.5, 167.7, 162.1 (3×CO), 136.4, 130.6, 129.7, 129.5 (C-2,6,8,9), 122.5, 118.8, 112.3, 108.4 (C-3,4,5,7), 82.6 (OCMe3), 52.2 (OCH3), 42.7 (CONHCH2), 28.1 (t-Bu). Anal. (C17H20N2O5) C,H,N.
Sources & evidence
- ORD record
- ord-0a571faa59864949a8ad5ffede124171
- Source dataset
- uspto-grants-1999_11
- Patent number
- US05985909
Reaction notes
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