Acetonitrile → HCID 86592513, compound

Participants

Reaction Conditions

Reaction Steps

A solution of n-butyllithium in hexane (1.56M, 68 ml, 0.11 mmol) was added at −70° C. to a solution of allyl(2S)-2-{[(aminocarbonyl)oxy]methyl}-4-(2-mercapto-1,3-thiazol-4-yl)-3,6-dihydro-1(2 H)-pyridinecarboxylate (37.8 mg, 0.11 mmol) in THF (1 ml)/DMF (0.5 ml). The mixture was warmed to 0° C. and then stirred for 15 minutes. To the reaction solution was added at 0° C. a solution of allyl (4R,5R,6S)-3-[(diphenoxyphosphino)oxy]-4-methyl-7-oxo-6-{(1R)-1-[(trimethylsilyl)oxy]ethyl}-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate in acetonitrile (30%, 0.42 g, 0.22 mmol) and the solution was allowed to stand in a refrigerator for 13 hours. To the reaction solution was added ice water and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. After removal of the solvent in vacuo, the residue was purified with silica gel chromatography (hexane/ethyl acetate) to give crude allyl (4R,5S,6S)-3-{[4-((2S)-1-[(allyloxy)carbonyl]-2-{[(aminocarbony)oxy]methyl}-1,2,3,6-tetrahydro-4-pyridinyl)-1,3-thiazol-2-yl]sulfanyl}-4-methyl-7-oxo-6-{(1R)-1-[(trimethylsilyl)oxy]ethyl}-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (154 mg).

Provenance & Evidence