Hydroxylamine → tert-butyl N-[(1S)-1-(hydroxycarbamoyl)-3-(methylsulfanyl)propyl]carbamate

Participants

Reaction Steps

A solution of (S)-methyl 2-(tert-butoxycarbonylamino)-4-(methylthio)butanoate (1 g, 3.8 mmol) in dioxane (10 mL) and hydroxylamine (50% in water, 10 mL) was stirred at room temperature for 2 days. The solution was diluted with ethyl acetate (200 mL). The organic layer was washed with 1N HCl, brine, and dried over sodium sulfate, filtered and concentrated to give a residue, which was purified on silica gel column (hexane:ethyl acetate, 1:1 to pure acetate) to give (S)-tert-butyl 1-(hydroxyamino)-4-(methylthio)-1-oxobutan-2-ylcarbamate as a white solid (0.33 g, 33%). MS calcd for (C10H20N2O4S+H)+: 265.1; MS found: (M+H)+=266.2, 166.2 (-Boc).

Provenance & Evidence