Hydrochloric Acid → HCID 86614040, compound

Participants

Reaction Steps

To a stirred suspension of (1S,2R,4aS,5S,8R,8aR)-2-(acetyloxy)-8a-hydroxy-5-isopropyl-3,8-dimethyl-1,2,4a,5,6,7,8,8a-octahydro-1-naphthalenyl-(2S,3aR,9bR)-6-chloro-9b-hydroxy-5-methyl-1,2,3,3a,5,9b-hexahydropyrrolo[2,3-c][2,1]benzoxazine-2-carboxylate (Example 1, 887 mg) in methanol (25 ml) was added a solution of concentrated hydrochloric acid (1 ml) in methanol (25 ml). After 4 days the reaction mixture was diluted with dichloromethane (150 ml) and washed with water (3×100 ml). The combined aqueous layers were washed with dichloromethane (25 ml). All the organic phases were combined, dried and concentrated to yield a yellow solid (802 mg). Purification was achieved by flash column chromatography on silica gel eluting with 1:1 ethyl acetate:hexane to give the product (604 mg).

Provenance & Evidence