Water → p-Nitrobenzyl (5RS,6SR)-3-(2-acetamidoethylthio)-6-[(1RS)-1-p-nitrobenzyloxycarbonyloxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

Participants

Reaction Steps

p-NItrobenzyl (5RS, 6SR)-6-[(1RS)-1-p-nitrobenzyloxycarbonyloxyethyl]-3-(2-pyrimidylsulphinyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (15 mg) in dichloromethane (2 ml) was cooled in an ice-bath and treated with benzyldimethyl-n-hexadecylammonium chloride (1.1 mg), followed by 2-acetamidoethanethiol (3 mg) in dichloromethane (1 ml), followed by water (1 ml), followed by 0.1M aqueous NaOH (0.25 ml). After stirring in the cold for 30 min. the reaction mixture was allowed to warm to room temperature and stirred for 1.5 h. After dilution with CH2Cl2 /H2O and separation, the dichloromethane layer was dried (MgSO4) and evaporated in vacuo. The residue was chromatographed on silica gel, eluting with ethyl acetate, followed by ethylacetate/ethanol (95:5) to give the title compound νmax. (CH2Cl2) 3450, 1790, 1750, 1700(sh), 1680, 1525, 1350 cm-1.

Provenance & Evidence