Sodium Hydroxide → HCID 18368062, compound

Participants

Reaction Steps

To a solution of 2-(4-acetoxymethyl-2-furoyl)-6-chloro-1-ethoxycarbonyl-3-(propionylamino)indole (step 1, 114 mg, 0.313 mmol) in ethanol (2 ml) was added 2N aqueous sodium hydroxide (2 ml). After stirring for 3 h, the mixture was poured into saturated aqueous ammonium chloride (20 ml) and extracted with ethyl acetate (80 ml). The organic layer was washed with brine (20 ml), dried (MgSO4) and concentrated. The residue was purified by flash column chromatography eluting with ethyl acetate/hexane (1/1) and recrystalization from 2-propanol/isopropyl ether to give 46 mg (40%) of the titled compound as yellow solids. m.p.: 171-172° C. 1H-NMR (CDCl3) δ: 10.74 (1H, br s), 9.37 (1H, br s), 8.45 (1H, d, J=9.06 Hz), 7.08 (1H, s), 7.42 (1H, s), 7.36 (1H, d, J=1.81 Hz), 7.06 (1H, dd, J=9.06 Hz, 1.81 Hz), 4.67 (2H, s), 2.58 (2H, q, J=7.58 Hz), 1.33 (3H, t, J=7.58 Hz).

Provenance & Evidence