Acetic Acid Mixture with Hydrobromic Acid → HCID 53747170, compound

Participants

Reaction Conditions

Reaction Steps

A solution comprised of tert-butyl(S)-3-diazo-2-oxo-1-phenethylpropylcarbamate (7.09 g, 23.4 mmol) in ether (100 mL) was cooled to −10° C. and a solution comprised of hydrogen bromide/acetic acid (4.66 mL, 30% by weight) in ether (30 mL) was added dropwise. The mixture was stirred for 30 minutes and then ether (200 mL) was added. The mixture was washed with brine (50 mL), saturated aqueous sodium bicarbonate (150 mL), brine (50 mL), dried (MgSO4), filtered, and concentrated. Product was crystallized from hexane, to provide tert-butyl (S)-3-bromo-2-oxo-1-phenethylpropylcarbamate (5.29 g, 14.7 mmol). 1H NMR (CDCl3): δ 1.44 (9H, s, t-Bu), δ 1.86 (1H, m, one CH2CH2C6H5), δ 2.18 (1H, m, other CH2CH2C6H5), δ 2.67 (2H, t, J=7.7 Hz, CH2CH2C6H5), δ 3.99 (2H, 2×d, J=13 Hz, CH2Br), δ 4.53 (1H, m, CHNH), δ 5.08 (1H, br.D, 5 Hz, NH), δ 7.17-7.29 (5H, m, aromatic H).

Provenance & Evidence