Sodium Bicarbonate → HCID 86745148, compound

Participants

Reaction Steps

A solution of the crude bis tetrahydropyranyl ether of Step C in formic acid, (16 ml), H2O (30 ml) and THF (35 ml) is stirred for 24 h at room temperature. The mixture is cooled in an ice-water bath, H2O (30 ml) is added, and solid NaHCO3 is added till a pH of 7 is reached. The aqueous layer is extracted with ether, the combined organic layers are washed with saturated NaHCO3 and brine, dried over MgSO4 and concentrated in vacuo. Column chromatograph separation on silica gel, eluting with 2% MeOH in AcOEt, gives (8R,11R,12R,15R,16R)-11,15-dihydroxy-16-methyl-l6-methoxy-9-oxo-prost-13-en-1-oic acid, methyl ester which solidifies in the freezer (m.p. 44-45° C.).

Provenance & Evidence