Chlorotrimethylsilane → HCID 67837029, compound

Participants

Reaction Steps

To a solution of (3S,4R)-4-[2-(1-benzyloxycarbonyl-1,2,3,6-tetrahydropyridine-4-yl)-2-oxoethyl]-3-[(1R)-1-hydroxyethyl]-2-oxoazetidine (3.59 g) and pyridine (3.9 ml in dichloromethane (3.5 ml) was added dropwise trimethylsilyl chloride (1.42 ml) at -70° C. under nitrogen atmosphere and the mixture was stirred for 1 hour. To this solution was added dropwise at -70° C. a reaction mixture of oxalyl chloride (1.26 ml) and 4-nitrobenzyl alcohol (2.3 g) in dichloromethane (10 ml) at 0° C., which solution was stirred for additional 1 hour. The reaction mixture was poured into a mixture of ethyl acetate (70 ml) and water (40 ml). The organic layer was separated, washed with water (50 ml) containing acetic acid (550 μl), and brine (50 ml) successively, and then dried over magnesium sulfate. Evaporation of the solvent gave a residue, which was chromatographed on silica gel (250 ml) eluting with a mixture of hexane and ethyl acetate (1:1, V/V) to give 4-nitrobenzyl 2-[(3S,4R)-4-{ 2-(1-benzyloxycarbonyl-1,2,3,6-tetrahydropyridin-4-yl)-2-oxoethyl}-3-{(1R)-1-trimethylsilyloxyethyl}-2-oxoazetidin-1-yl]-2-oxoacetate (4.73 g).

Provenance & Evidence