Potassium Carbonate → HCID 86626198, compound

Participants

Reaction Steps

To a solution of the above (S)-tert-butyl 4-methoxy-4-methyl-1-(methylamino)pentan-2-ylcarbamate (˜2.99 mmol) in acetone (9 mL) and water (3 mL), there was added K2CO3 (1.24 g, 9.0 mmol), followed by Teoc-OSu (0.85 g, 3.29 mmol). The resulting mixture was stirred at rt until no starting material remained (˜1 h). Acetone was removed under vacuum, and the aqueous residue was extracted with CH2Cl2 (4×5 mL). The combined organic layers were concentrated, and crude residue was purified with flash column chromatography to give (S)-tert-butyl 4-methoxy-4-methyl-1-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)pentan-2-ylcarbamate (0.18 g, 15%, 3 steps) as a clear oil. 1H NMR (400 MHz, CDCl3): 4.82, 4.92 (br, 1 H), 4.16 (m, 2 H), 3.88 (m, 1 H), 3.44 (m, 1 H), 3.24 (m, 1 H), 3.16 (s, 3 H), 2.88, 2.90 (s, 3 H), 1.44 (s, 9 H), 1.18, 1.20 (s, 6 H), 0.98 (m, 2 H), 0.02 (s, 9 H); MS m/z 405 (M+H+).

Provenance & Evidence