Phenylacetic Acid → 4-benzyloxy-N-[2-oxo-2-(4-phenylacetyl-piperazin-1-yl)-ethyl]-benzamide

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Reaction Steps

EDCI.HCl (122 mg, 0.634 mmol), HOBT (68 mg, 0.51 mmol) and DIPEA (220 μL, 1.27 mmol) were added to a mixture of 4-benzyloxy-N-(2-oxo-2-piperazin-1-yl-ethyl)-benzamide (150 mg, 0.42 mmol), DMF (5 mL) and phenyl acetic acid (69 mg, 0.51 mmol). The resulting mixture was allowed to stir at room temperature overnight. Water was then added, and the product was extracted using EtOAc. The organic phase was washed with brine, dried over Na2SO4 and concentrated under reduced pressure to afford a crude product, which was purified twice by column chromatography (using silica gel with a mesh size of 60-120, and 80:20 EtOAc:hexane as the eluent) to afford 4-benzyloxy-N-[2-oxo-2-(4-phenylacetyl-piperazin-1-yl)-ethyl]-benzamide in 55% yield. LC-MS purity: 92% 1H NMR (DMSO-D6): δ 8.4 (t, 1H), 7.8 (d, 2H), 7.4 (m, 7H), 7.2 (d, 3H), 7.1 (d, 2H), 5.2 (s, 2H), 4.1 (d, 2H), 3.8 (d, 2H), 3.5 (m, 8H).

Provenance & Evidence