Methanol → HCID 23047431, compound

Participants

Reaction Steps

A mixture of sodium hydroxide (120 mg), water (2 ml), methanol (10 ml) and ethyl (E)-3-hydroxy-7-(3-isopropyl-1-phenylpyrrolo[2,1-a]isoquinolin-2-yl)-5-oxohept-6-enoate (230 mg; prepared as described in Example 4) was stirred under an argon atmosphere at the ambient temperature for 5 hours. Water (10 ml) was added and the solution was acidified to pH 5 by treatment with glacial acetic acid. The milky solution was extracted with diethyl ether (4×50 ml) and the combined extracts were dried over magnesium sulphate and evaporated, to give (E-3-hydroxy-7-(3-isopropyl-1-phenylpyrrolo[2,1-a]isoquinolin-2-yl)-5-oxohept-6-enoic acid, (80 mg) in the form of a buff foam, m.p. 95°-100° C. [Elemental analysis: C 76.7; H, 6.57; N, 3.02%; Calculated: C, 76.2; H, 6.16; N, 3.2%. N.M.R. (in CDCl3 and D2O): 1.56 (6H, d, J=7 Hz), 2.54 (2H, d, J=7 Hz), 2.55 (2H, d, J=7 Hz), 3.76 (1H, septet, J=7 Hz), 4.42 (1H, quintet, J=7 Hz), 5.68 (1H, d, J=16 Hz), 6.75 (1H, d, J=8 Hz), 7.03-7.57 (9H, m), 7.84 (1H, d, J=8 Hz), 7.86 (1H, d, J=16 Hz)].

Provenance & Evidence