Hydrochloric Acid → HCID 10480187, compound

Participants

Reaction Steps

In 4 ml of methylene chloride was suspended 380 mg of ethyl 10-(1-benzyloxycarbonylaminocyclopropyl)-9-fluoro-3-hydroxymethyl-7-oxo-2,3-dihydro-7H-pyrido[1,2,3de][1,4]benzoxazine-6-carboxylate. To the resulting suspension were added, with ice-cooling, 230 mg of triethylamine and 260 mg of methanesulfonyl chloride in this order. The resulting mixture was stirred at room temperature for 30 minutes. To the reaction mixture were added 10 ml of methylene chloride and 10 ml of water in this order. The resulting mixture was adjusted to pH 1 with 2N hydrochloric acid. The organic layer was separated, washed with water and a saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. To the residue obtained were added 4.4 ml of benzene and 175 mg of 1,8-diazabicyclo-[5,4,0]undec-7-ene in this order. The resulting mixture was refluxed for 1 hour. The reaction mixture was added to a mixture of 20 ml of ethyl acetate and 20 ml of water. The resulting mixture was adjusted to pH 1 with 2N hydrochloric acid. The organic layer was separated, washed with water and a saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue obtained was purified by a column chromatography (eluant: toluene/ethyl acetate=3/2) to obtain 260 mg (yield: 71.0%) of ethyl 10-(1-benzyloxycarbonylaminocyclopropyl)-9-fluoro-3-methylene-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]-benzoxazine-6-carboxylate.

Provenance & Evidence