Sodium Hydroxide → HCID 9938977, compound

Participants

Reaction Conditions

Reaction Steps

A stirred solution of ethyl 3-(4-benzoyl-1-{[3-methoxy-4-(3-o-tolyl-ureido)-phenyl]-acetyl}-1,2,3,4-tetrahydro-quinoxalin-6-yl)-butanoate [0.124 g, Reference Example 16(a)] in methanol (5 ml) was treated with sodium hydroxide solution (764 μl, 15%). The resulting mixture was heated to reflux for 30 minutes, then cooled to 40° C. and then evaporated (40 mbar, 40° C.). The residue was treated with distilled water (40 ml) and the aqueous solution was washed three times with ether (20 ml), then treated with hydrochloric acid (4 ml, 1M) and then extracted three times ethyl acetate (25 ml). The combined extracts were dried over magnesium sulfate then evaporated to dryness (40 mbar, 40° C.). The crude residue (91 mg) was subjected to preparative thin layer chromatography on silica(20×20 cm plates, 0.25 mm thickness) eluting with a mixture of dichloromethane and methanol (9:1, v/v) to give the title compound as a white powder (15 mg). 1H NMR (400 MHz, (CD3)2SO, at a temperature of 373° K.]: δ0.92 (d, J=7 Hz, 3H); 2.16 (d, J=7.5 Hz, 2H); 2.27(s, 3H); 2.80 to 3.05 (m, 1H); 3.84 (s, 3H); 3.94 (m, 2H); 3.96 (s, 2H); 4.01 (m, 2H); 6.60 (broad s, 1H); 6.76 (broad d, J=8 Hz, 1H); 6.88 (broad s, 1H); 6.95 to 7.05 (m, 2H); 7.10 to 7.20 (m, 4H); 7.33 (broad t, J=7.5 Hz, 2H); 7.40 (broad t, J=7.5 Hz, 1H); 7.56 (d, J=8 Hz, 1H); 7.68 (broad d, J=8 Hz, 1H); 8.04 (d, J=8.5 Hz, 1H); 8.23 (broad s, 1H); 8.29 (broad s, 1H). MS (ES): 621 (MH+).

Provenance & Evidence