Ammonia → 3-(5-Hydroxy-4,6,7-trimethyl-benzo[1,3]oxathiol-2-yl)-propionamide

Participants

Reaction Steps

4.9 g of methyl 3-[5-(3-methoxycarbonylpropionyloxy)-4,6,7-trimethyl-1,3-benzoxathiole-2-yl]propionate (prepared as described in Example 31) was dissolved in 60 ml of methanol, and 17 g of 28% w/v aqueous ammonia was added to the solution. The reaction mixture was then allowed to react for 5 days at room temperature. At the end of this time, the solvent was distilled off under reduced pressure, and the residue was dissolved in ethyl acetate. The resulting solution was washed with water and dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure. The resulting crude product was subjected to silica gel column chromatography, and the title compound, melting at 160°-161° C., was obtained from the fraction eluted with a 3:7 by volume mixture of benzene and ethyl acetate. Mass spectrum (m/e): 267 (M+).

Provenance & Evidence