3-(4-Hydroxyphenyl)propionic acid → 2-[3-(4-Hydroxyphenyl)propionylamino]acetic acid ethyl ester

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Reaction Steps

DIPEA (390 mg, 0.52 mL, 3.02 mmol) was added to a stirred solution of 3-[4-hydroxy phenyl]propionic acid (100 mg, 0.60 mmol) in DMF (10 mL). HOBT (90 mg, 0.67 mmol) and EDCI.HCl (290 mg, 1.51 mmol) were added at room temperature. After 2 minutes glycine ethyl ester hydrochloride (100 mg, 0.72 mmol) was added. The resulting mixture was stirred at room temperature for 48 hours. 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 196 mg of [3-(4-hydroxy-phenyl) propionylamino]-acetic acid ethyl ester. 1H NMR (CDCL3): δ 7 (d, 2H), 6.65 (d, 2H), 6.0 (bs, 1H), 4.15 (q, 2H), 4.0 (d, 2H), 3.5 (s, 2H), 2.8 (t, 2H), 2.45 (t, 2H), 1.2 (t, 3H), LC-MS purity: 68.23%.

Provenance & Evidence