Acetic Anhydride → HCID 18606599, compound

Participants

Reaction Steps

A mixture of 3.2 g of (-)-cis-2,3-dihydro-5-[2-(dimethylamino)ethyl]-3-hydroxy-2-(4-methoxyphenyl)naphtho[1,8-bc]-1,5-thiazocin-4(5H)-one hydrochloride and 60 mL of acetic anhydride was stirred under nitrogen at 100° for 17 hours. The excess reagent was removed under reduced pressure and to the residue ice-water was added. The resulting suspension was made basic with concentrated ammonium hydroxide and extracted with ethyl acetate (2×50 mL). The combined extracts were washed with brine (50 mL) and dried (magnesium sulfate). Removal of the solvent under reduced pressure gave 3.2 g (99%) of (-)-cis-3-(acetyloxy)-2,3-dihydro-5-[2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)naphtho[1,8-bc]-1,5-thiazocin-4(5H)-one as an amorphous compound, [α]D25 -190.81° (C 0.48, methanol).

Provenance & Evidence