Triethylamine → 3-[(4S,5S)-3-benzyloxycarbonyl-4-isobutyl-2,2-dimethyloxazolidin-5-yl]-2-[2-(2-tetrahydropyranyloxy)ethyl]-2-propenoic acid methylamide

Participants

Reaction Conditions

Reaction Steps

45 mg of 3-[(4S,5S)-3-benzyloxycarbonyl-4-isobutyl-2,2-dimethyloxazolidin-5-yl]-2-[2-(2-tetrahydropyranyloxy)ethyl]-2-propenoic acid was dissolved in 0.3 ml of dry dimethylformamide, and 3.71 mg of methylamide, 32.9 mg of diphenylphosphorylazide and 12.1 mg of triethylamine were added thereto at -10° C. under stirring. Then, the mixture was stirred at -10° C. for one hour and at room temperature overnight. To the reaction solution, 20 ml of ethyl acetate was added. The ethyl acetate layer was washed sequentially with a 10% citric acid aqueous solution, water, a 4% sodium hydrogencarbonate aqueous solution, water and a saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (Kieselgel 60) by using a mixture of chloroform/methanol (5/1) to obtain 17.5 mg of 3-[(4S,5S)-3-benzyloxycarbonyl-4-isobutyl- 2,2-dimethyloxazolidin-5-yl]-2-[2-(2-tetrahydropyranyloxy)ethyl]-2-propenoic acid methylamide as a colorless oily substance.

Provenance & Evidence