Water → HCID 178431670, compound

Participants

Reaction Steps

Under inert gas, 2.58 ml of a 0.5 N zinc chloride solution in THF were cooled to −78° C., and 0.48 ml of a 1.8 N phenyllithium solution in dibutyl ether was added dropwise. The reaction solution was allowed to come to room temperature and stirred for 30 minutes. Then this solution was added to a solution of 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 and 14.1 mg of dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium in 2 ml of THF. After stirring at 60° C. for 45 minutes, the reaction was allowed to cool to room temperature, 10 ml of water and 10 ml of ethyl acetate were added, and the organic phase was dried over MgSO4 and concentrated by rotary evaporation. The residue was dissolved in 1.5 ml of methanol, 0.15 ml of concentrated hydrochloric acid was added and the mixture was stirred at room temperature for 16 hours. The reaction solution was diluted with ethyl acetate and washed with saturated aqueous sodium chloride solution, dried over MgSO4 and concentrated by rotary evaporation. The residue was purified in a purification laboratory by means of preparative HPLC. The product-containing fractions were combined, the acetonitrile was removed under reduced pressure, and the aqueous residue was basified with saturated aqueous sodium hydrogencarbonate solution and extracted with dichloromethane. The organic phase was dried over MgSO4 and concentrated by rotary evaporation, and the residue was taken up again in a mixture of acetonitrile and water and lyophilized. This gave the product (57.8 mg) with a molecular weight of 464.6 g/mol (C26H28N2O4S); MS (ESI): m/e=565 (M+H+).

Provenance & Evidence