Methanol → Benzyl 4-mercapto-2-methylbutan-2-ylcarbamate

Participants

Reaction Steps

S-3-(Benzyloxycarbonylamino)-3-methylbutyl ethanethioate (3.00 g, 10.2 mmol) was dissolved into methanol (100 mL). Sodium hydroxide solution (5 N, 6.1 mL, 30.6 mmol) was added to the solution in one portion and stirred at room temperature for 1 hour. Thin-layer chromatography (40% ethyl acetate in hexanes) analysis of reaction mixture indicated all the starting material was consumed. The organic solvent was removed and the resulting aqueous solution was made acidic (˜pH 5) with 1 N HCl, while cooled in an ice bath. The aqueous suspension was extracted with ethyl acetate (2×100 mL) and the combined organic layer washed with water (50 mL) and brine (50 mL), dried over anhydrous MgSO4, filtered and concentrated to a pale yellow oil (2.83 g, quant). The material was used without further purification. 1H NMR (CDCl3, 400 MHz): δ 1.29 (s, 6H), 2.02 (m, 2H), 2.48-2.5 (m, 2H), 2.83 (t, 20 Hz, 2H), 3.60 (t, 20 Hz, 2H), 4.63 (br s, 2H), 5.05 (s, 2H), 7.29-7.37 (m, 5H). LRMS (ESI/APCI) m/z 316 [M+H]+.

Provenance & Evidence