Methanol → HCID 15157461, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 250 mg (0.515 mmol) of the titled product of Example 17, 153 mg (2.06 mmol) of glycidol, and 9 mg of a 40% solution of benzyl-trimethylammonium hydroxide in methanol in 2.5 ml of dimethyl formamide under argon was stirred overnight at 70° C. After addition of another 153 mg of glycidol and one drop of 40% methanolic benzyltrimethylammonium hydroxide, the temperature was raised to 85°-90° C. with stirring. After stirring for 7 hours, the mixture was permitted to cool and was then partitioned between ethyl acetate and water. The aqueous layer was further extracted twice with ethyl acetate. The combined organic extracts were washed with brine, dried (Na2SO4), the drying agent removed by filtration, and the solvent removed on a rotary evaporator. The residue was chromatographed on a silica gel column. Elution with 10% methanol/2.5% acetic acid/87.5% ethyl acetate as eluent afforded, after drying under vacuum for eight hours, the title product (170 mg), which was isolated as the hemihydrate.

Provenance & Evidence