Trimethylaluminum → N-[(1S)-3-[tert-butyl(dimethyl)silyl]oxy-1-phenylpropyl]-6,6-dimethyl-5-(3-methylphenyl)-4,4-dioxo-5H-1,4,3-oxathiazin-2-amine

Participants

Reaction Steps

Under inert gas, 100 mg of [5-(3-bromophenyl)-6,6-dimethyl-4,4-dioxo-5,6-dihydro-4H-4lambda6-1,4,3-oxathiazin-2-yl]-[(S)-3-(tert-butyldimethylsilanyloxy)-1-phenylpropyl]amine, 8 mg of bis(dibenzylideneacetone)palladium and 19.6 mg of 1,2,3,4,5-pentaphenyl-1-(di-tert-butylphosphino)ferrocene were initially charged, dissolved in 3 ml of toluene and stirred at room temperature for 5 minutes. After the addition of 0.17 ml of a 2 N solution of trimethylaluminum, the reaction mixture was stirred at 70° C. for 1.5 hours. After cooling to room temperature, the solvent was removed under reduced pressure and the residue was purified by means of normal phase chromatography using a Flashmaster with an n-heptane/ethyl acetate gradient. The product-containing fractions were combined and concentrated by rotary evaporation. This gave the product (51.7 mg) with a molecular weight of 516.8 g/mol (C27H40N2O4SSi); MS (ESI): m/e=517 (M+H+).

Provenance & Evidence