Pivaloyl chloride → HCID 14460310, compound

Participants

Reaction Conditions

Reaction Steps

1.1 ml of 1 M lithium bis(trimethylsilyl)-amide are added at -70° C. with stirring in the course of 5 minutes to a mixture of 275 mg (0.515 mmol) of p-nitrobenzyl 2-[4-methylthio-3-(1-(p-nitrobenzyloxycarbonyloxy)-ethyl)-2-oxoazetidinyl]-acetate and 67 μl (0.55 mmol) of pivaloyl chloride in 6.7 ml of dry tetrahydrofuran and the reaction mixture is stirred at -70° C. during the course of a further 30 minutes and then diluted with 40 ml of toluene and with 30 ml of 2 N HCl, then washed twice with 40 ml each of NaCl solution. The organic phase is dried over MgSO4 and filtered, and the solvent is removed in vacuo. The residue is chromatographed on 10 g of silica gel using toluene/ethyl acetate (9:1), 268 mg of a white non-crystalline solid being obtained. IR spectrum in CH2Cl2 : 2930, 2850, 1775, 1760, 1720, 1610, 1535, 1350 cm-1 .

Provenance & Evidence