monoMethyl succinate → HCID 86614041, compound

Participants

Reaction Steps

A mixture of (1S,2R,4aS,5R,8R,8aR)-2,8a-dihydroxy-3,8-dimethyl-5-(1-methylethenyl)-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl (2S,3aR,9bR)-6-chloro-9b-hydroxy-5-methyl-1,2,3,3a,5,9b-hexahydropyrrolo[2,3-c][2,1]benzoxazine-2-carboxylate (Preparation 139, 100 mg, 0.19 mmol), commercially available 4-(methyloxy)-4-oxobutanoic acid (50 mg, 0.38 mmol), 4-dimethylaminopyridine (60 mg, 0.5 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (90 mg, 0.58 mmol) and dichloromethane (5 ml) was stirred for 18 h and the reaction mixture concentrated in vacuo. The crude product was purified by chromatography on a Biotage® 12M column eluting with dichloromethane:diethyl ether (4:1). The pure fractions were combined and the solvent removed in vacuo to give the title product (23 mg, 18%).

Provenance & Evidence