4-(Benzyloxy)benzoic acid → (4-Benzyloxy-benzoylamino)-acetic acid ethyl ester

Participants

Reaction Steps

DIPEA (5.12 g, 6.85 mL, 0.59 mmol) was added to a stirred solution of 4-benzyloxy benzoic acid (2 g, 8.7 mmol) in DMF (18 mL). HOBT (1.3 g, 9.5 mmol) and EDCI.HCl (4.2 g, 21.7 mmol) were added at room temperature. After 2 minutes glycine ethyl ester HCl (1.47 g, 10.5 mmol) was added to the reaction mixture. 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 the crude product. Purification using column chromatography (silica gel of mesh size of 60-120 using 40% EtOAc in Hexane as eluent) afforded 2.47 g (90.1% yield) of (4-Benzyloxy-benzoylamino)-acetic acid ethyl ester. LCMS Purity %: 98.6, 1H NMR (DMSO): δ 8.9 (t, 1H), 7.8 (d, 2H), 7.5 (m, 5H), 7.2 (d, 2H), 5.4 (s, 2H), 4.2 (q, 2H), 4.0 (d, 2H), 0.8 (t, 3H).

Provenance & Evidence