Cyclopropanecarboxylic acid → HCID 91168875, compound

Participants

Reaction Steps

To a solution 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) and 4-dimethylaminopyridine (30 mg, 0.25 mmol) in tetrahydrofuran (10 ml) was added cyclopropanecarboxylic acid (400 mg, 4.7 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (90 mg, 0.58 mmol) and the resulting mixture stirred at room temperature for 18 h. The reaction mixture was passed through a Sepak® cartridge (silica, 1.5 g) to remove insoluble material and the solvent removed in vacuo. The crude product was purified to give the title compound (20 mg, 18%).

Provenance & Evidence