Water → HCID 21715989, compound

Participants

Reaction Steps

A solution of a 1:1 mixture of the erythro- and threo-diastereoisomers of (E)-3,5-dihydroxy-7-[4-(4-fluorophenyl)-2-isopropyl-1-oxo-1,2-dihydroisoquinolin-3-yl]hept-6-enoic acid (0.35 g; prepared as described in Example 5) in dichloromethane (25 ml) was treated with dicyclohexylcarbodiimide (0.18 g) and the resulting solution was stirred at room temperature for 1 hour. The solution was treated with water (20 ml), and stirred for 30 minutes. The layers were then separated and the aqueous phase was extracted with dichloromethane (210 ml). The combined extracts were dried over magnesium sulphate and evaporated to dryness. The resulting residue was triturated with diethyl ether (10 ml) and the insoluble material was filtered off. Evaporation of the ethereal solution gave a pale yellow solid, which was triturated with petroleum ether (b.p. 60°-80° C.; 10 ml) and filtered, to give (E)-4-hydroxy-6-[2-{4-(4-fluorophenyl)-2-isopropyl-1-oxo-1,2-dihydroisoquinolin-3-yl}ethenyl]-3,4,5,6-tetrahydro-2H-pyran-2-one, in the form of a pale yellow solid (0.21 g), m.p. 151°-154° C. [Elemental analysis: C, 70.8; H, 5.74; N, 3.35%; calculated: C, 71.24; H, 5.74; N, 3.32%].

Provenance & Evidence