Dichloromethane → tert-Butyl 4-[N-[2-Acetoxymethyl-4-oxo-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl]amino]benzoate

Participants

Reaction Steps

2-Acetoxymethyl-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-4,6-dione (0.140 g, 0.36 mmol) was suspended in anhydrous methanol (8 ml) and then anhydrous dichoromethane (4 ml) was added until a clear solution was obtained. Tert-butyl 4-aminobenzoate (0.084 g, 0.44 mmol) was then added followed by decaborane (0.014 g, 0.12 mmol). The reaction mixture was stirred overnight at room temperature under argon. The solvent was removed in vaciio, and the residue was purified by column chromatography on elution with 40% ethyl acetate in hexane. The product was obtained as a glass (0.127 g, 63%) 1H-NMR (CDCl3) 1.20 (s, 9H, POM C(CH3)3), 1.58 (s, 9H, CO2C(CH3)3), 2.20 (s, 3H, CH3CO), 2.02, 2.72 (2×m, 2H, 7-CH2), 3.13 (m, 2H, 8-CH2), 4.36 (d, J=7.7 Hz, 1H, NH), 5.15 (q, J=6.8 Hz, 1H, 6-H), 5.21 (s, 2H, 2-CH2), 6.12 (AB system, J=10.7 Hz, 2H, POM CH2), 6.67 (d, J=8.8 Hz, 2H, 3,5′-ArH), 7.57 (s, 1H, 9-H), 7.85 (d, J=8.9 Hz, 2H, 2′,6′-ArH), 8.25 (s, 1H, 5-H); MS (ESI, m/z) 564 (M+H)+.

Provenance & Evidence