Methyl chloroformate → HCID 69803216, compound

Participants

Reaction Steps

To a stirred mixture of H-phe(4-NO2)-OH (11.4 g, 50.0 mmol) and NaOH (2.0 g, 50.0 mmol) in water (450 mL) at 0° C. was added methylchloroformate (4.25 mL, 55.0 mmol) and NaOH (2.2 g in 45 mL water) simultaneously. 1N NaOH was then added to adjust PH ˜9. The reaction mixture was stirred at ambient temperature overnight, the pH was adjust to 10 by adding more aqueous NaOH and the mixture was extracted with ether (2×75 mL). The aqueous layer was acidified to a pH=3 with 5N HCl, and extracted with ethyl acetate (2×400 mL). The combined ethyl acetate layers were dried (MgSO4), filtered and concentrated under reduced pressure to provide the titled compound (12.3 g). MS (ESI (−)) m/e 267 (M−H)+; 1H NMR (300 MHz, DMSO-d6) 8.16 (d, 2H), 7.60-7.52 (m, 3H), 4.28-4.18 (m, 1H), 3.47 (s, 3H), 3.26-3.17 (m, 1H), 3.05-2.92 (m, 1H).

Provenance & Evidence