Acetic Acid → HCID 131716592, compound

Participants

Reaction Steps

This silylate (b) (2.1 g; 3.69 millimoles) is dissolved in tetrahydrofuran (10 ml), mixed with acetic acid (0.8 ml) and tetrabutylammonium fluoride trihydrate (2.78 g; 2.4 equivalents) and kept at room temperature two nights. The reaction mixture is poured into aqueous sodium hydrogen carbonate-ethyl acetate. The organic layer is separated, washed with water, dried, and concentrated in vacuum, and purified by chromatography (Lober B, ethyl acetate) to give 6α-(1-hydroxyethyl)-1-methyl-2-(4-pyridylthio)methyl-1-carbapen-2-em-3-carboxylic acid p-methoxybenzyl ester (b) (455 mg; Yield: 27.1%; having physical constants as follows from polar fraction) and 6α-(1-hydroxyethyl)-1-methyl-2-(4-pyridylthio)methylidene-1-carbapenam-3-carboxylic acid p-methoxybenzyl ester (100 mg; Yield: 6.0%, from less polar fraction). IR (CHCl3)ν: 3400-3120br, 1750br, 1604, 1575 cm-1.

Provenance & Evidence