Acetyl chloride → Methyl 3-nitro-L-tyrosinate--hydrogen chloride (1/1)

Participants

Reaction Steps

Acetyl chloride (8.9 ml, 125 mmol) was added slowly to methanol (100 ml) at 0°. 3-Nitro-L-tyrosine (5.65 g, 25 mmol) was added and the mixture refluxed for 2 h. The solvent was evaporated in vacuo and the yellow solid obtained recrystallised from methanol to give the title compound as yellow needles (2.97 g, 43%), m.p. 200-201°. (Found: C, 43.29;H, 4.69; N, 10.19. C10H12N2O5HCl requires C, 43.41;H, 4.74; N, 10.13%); δH (CD3OD) 8.00 (1H, d, J 2.2 Hz, ArH), 7.53 (1H, dd, J 2.3, 8.6 Hz, ArH), 7.17 (1H, d, J 8.6 Hz, ArH), 4.37 (1H, dd, J 6.4, 7.0 Hz, CHα), 3.83 (3H, s, CO2CH3), 3.29 (1H, dd, J 6.3, 14.6 Hz, CHAHBAr) and 3.20 (1H, dd, J 7.1, 14.6 Hz, CHAHBAr); m/z (ES, 27V) 241 (M+ +1).

Provenance & Evidence