4-Nitrobenzoic Acid → HCID 10994638, compound

Participants

Reaction Steps

5.82 g (11.7 mmole) of (3S)-3-acetoxymethyl-5-[1-(methoxycarbonyl)ethyl]amino-6-benzyloxy-1-t-butoxycarbonylindoline, 5.24 g (23.4 mmole) of palladium acetate, 1.52 g (17.5 mmole) of manganese dioxide, and 1.95 g (11.7 mmole) of 4-nitrobenzoic acid were heated in 500 ml of dimethylacetamide at 90° C. for 18 hours. The reaction mixture was concentrated, ethyl acetate was added to the obtained residue, insoluble matter was removed by filtration, and the obtained filtrate was concentrated to give a residue. The residue was then purified by silica gel column chromatography with changing an eluate from benzene:ethyl acetate (5:1) to benzene:ethyl acetate (10:1) to give 1.34 g of methyl (1S)-1-acetoxymethyl-5-benzyloxy-3-t-butoxycarbonyl-1,2,3,6-tetrahydropyrrolo[3,2-e]indole-7-carboxylate. Yield, 23%. Mp. 128.5-129.5° C. (isopropyl ether). Elemental analysis: Calculated as C27H30N2O7 : C,65.57; H,6.11; N,5.66 Found: C,65.40; H,6.05; N,5.64 NMR (CDCl3) δ: 1.58 (9H, s), 2.10 (3H, s), 3.80-3.92 (2H, m), 3.92 (3H, s), 4.06 (1H, t, J=10.3 Hz), 4.15 (1H, dd, J=9.3, 11.2 Hz), 4.48 (1H, dd, J=5.4, 10.8 Hz), 5.22 (2H, s), 7.13 (1H, d, J=2.4 Hz), 7.39-7.48 (5H, m), 7.82 (1H, brs), 9.00 (1H, s). [α]D25 =-11.1° (c 0.21, methanol).

Provenance & Evidence