Aspirin → HCID 3362775, compound

Participants

Reaction Steps

DIPEA (0.288 mL, 1.67 mmol) was added dropwise to 2-acetoxy benzoic acid (100 mg, 0.56 mmol) in DMF (5 mL). EDCI (266 mg, 1.39 mmol) and HOBT (90 mg, 0.67 mmol) were added consecutively and after 10 mins, glycine ethyl ester. HCl (92 mg, 0.67 mmoles) was added. The resulting mixture was stirred at room temperature overnight. Water was then added, and the product was extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure to afford (2-Acetoxy-benzoyl amino)-acetic acid ethyl ester in 97% yield. 1H NMR (DMSO-D6): δ 12.2 (s, 1H), 9.2 (t, 1H), 7.9 (dd, 1H), 7.4 (dt, 1H), 6.9 (d, 2H), 4.2 (q, 2H), 4.1 (d, 2H), 3.8 (d, 1H), 1.3 (t, 3H).

Provenance & Evidence