Methanol → HCID 14554271, compound

Participants

Reaction Conditions

Reaction Steps

2.56 g of 4-methoxybenzyl 7β-phenylacetamido-3-[(Z)-3-chloro-1-propenyl]-3-cephem-4-carboxylate [IR υ max(Nujol)cm-1 : 3265, 1759, 1719, 1661, 1612, 1250, 1221, 1175, 1101, 1036, 824. NMR δ(CDCl3)ppm: 3.20, 3.44(2 H, ABq, J=18), 3.56(2 H, s), 3.71(3 H, s), 3.72(2 H, m), 4.87(1 H, d, J=4.5), 5.03(2 H, s), 5.4-5.9(2 H, m), 6.12(1 H, d, J=11), 6.30(1 H, d, J=9), 6.73(2 H, d, J=8.5), 7.15(5 H, s), 7.17(2 H, d, J=8.5)] was dissolved in 75 ml of dry methylene chloride and the solution was cooled to -40 ° C. 0.68 ml of pyridine and 1.35 g of PCL5 were successively added thereto with stirring. The resulting solution was stirred at room temperature for 2.5 hours and cooled to -40° C. and 46.5 ml of MeOH was dropwise added thereto. The resulting solution was stirred at room temperature for 1.5 hours, and neutralized with an aqueous NaHCO3 solution. The organic layer was washed with brine and water and dried over Na2SO4. After evaporation of the solvent, the residue was purified by silica gel column chromatography (60 g) with a mixture of benzene and ethyl acetate (1/1 volume) to give 1.0 g (51% yield) of 4-methoxybenzyl 7β-amino-3-[(Z)-3-chloro-1-propenyl]-3-cephem-4-carboxylate.

Provenance & Evidence