p-Toluenesulfonic acid → HCID 86758783, compound

Participants

Reaction Steps

A solution comprised of anhydrous p-toluenesulfonic acid (26 mmol) in ethyl ether (10 mL) was added to a suspension comprised of tert-butyl (S)-3-nitro-2-oxo-1-phenethylpropylcarbamate (4.5 g, 14 mmol) in dichloromethane (20 mL) and ethyl ether (150 mL). The mixture was stirred for 70 hours at room temperature and the filtered. The solid collected was washed thoroughly with ethyl ether and dried in vacuo to provide (S)-3-amino-1-nitro-5-phenylpentan-2-one p-toluenesulfonic acid salt (5.4 g, 13.7 mmol) as a white solid. 1H NMR (270 MHz, DMSO-d6): δ 1.92-2.05 (m, 1H), δ 2.15-2.28 (m, 1H), δ 2.29 (s, 3H), δ 2.56-2.76 (m, 2H), δ 4.44 (br.s, 1H), δ 6.97 (d, J=16.1 Hz, 1H), δ 6.29 (d J=16.1 Hz, 1H), δ 7.12 (d, J=8.4 Hz, 2H), δ 7.20-7.35 (m, 5H), δ 7.49 (d, J=8.2 Hz, 1H), δ 8.46 (br.s, 3 NH).

Provenance & Evidence