Diethyl Ether → N-{(S)-6-[(S)-1-((R)-2-Methylpropane-2-sulfinylamino)ethyl]-1,2,3,4-tetrahydro-naphthalen-2-yl}-4-[(S)-1-(tetrahydrofuran-2-yl)methoxy]benzamide

Participants

Reaction Steps

A suspension, cooled to −45° C., of N-((S)-6-{[(E)-(R)-2-methylpropane-2-sulfinylimino]methyl}-1,2,3,4-tetrahydronaphthalen-2-yl)-4-[(S)-1-(tetrahydrofuran-2-yl)methoxy]benzamide (0.34 g), diethyl ether (15 ml) and dichloromethane (15 ml) was admixed with methylmagnesium bromide (1.1 ml; 1.4 M in toluene). After warming to room temperature, the mixture was stirred for another 5 hours. The reaction mixture was hydrolyzed cautiously with water and extracted with ethyl acetate. The organic phase was washed with sodium chloride solution, dried over sodium sulfate and concentrated. The residue was purified by chromatography on silica gel (eluent: ethyl acetate). The product was thus obtained with the molecular weight of 498.69 (C28H38N2O4S); MS (ESI): 499 (M+H+).

Provenance & Evidence