Sodium Hydroxide → HCID 23704065, compound

Participants

Reaction Steps

A solution of a 3:2 mixture of the erythro- and threo-isomers of ethyl (E)-3,5-dihydroxy-7-(3-isopropyl-1-phenylpyrrolo[2,1-a]phthalazin-2-yl)-hept -6-enoate (0.26 g; prepared as described in Example 1) and sodium hydroxide (22 mg) in water (1.0 ml) and methanol (10 ml) was stirred at the ambient temperature under an atmosphere of argon for 3 hours. The solution was then evaporated in vacuo and the residue was dried by treatment twice with methanol (2×10 ml) and once with diethyl ether (10 ml) followed each time by evaporation in vacuo, finally drying under high vacuum, to give sodium (E)-3,5-dihydroxy-7-(3-isopropyl-1-phenylpyrrolo[2,1-a]phthalazin-2-yl)-hept-6-enoate (0.21 g) in the form of a yellow solid, m.p. 209°-215° C. [Elemental analysis: C, 65.8; H, 6.1; N, 5.4; H2O, 4.9%; calculated for C27H27N2O4Na:1.5H2O: C, 65.7; H, 6.13; N, 5.7; H2O, 5.5%; NMR (in a mixture of DMSO-d6 and D2O): 1.10-1.32 (2 H, m), 1.5 (6 H, d, J=7 Hz), 1.7-2.1 (2 H, m), 3.50-3.86 (2 H, m), 4.02-4.16 (1 H, m), 5.28 and 5.36 (1 H, two dd, J=16 Hz, 6 Hz), 6.46 (1 H, dd, J=16 Hz, 1 Hz), 7.16-7.60 (8 H, m), 7.78-7.88 (1 H, m), 8.57 (1 H, s)].

Provenance & Evidence