Water → 2-Benzyloxy-6-(4-tert-butoxycarbonylaminobutoxy)-benzoic Acid Methyl Ester

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Reaction Steps

To a solution of 2-(4-tert-butoxycarbonylaminobutoxy)-6-hydroxybenzoic acid methyl ester (1.5 g, 4.4 mmol) in DMF (20 mL) is added benzyl bromide (0.56 mL, 4.6 mmol) and K2CO3 (1.8 g, 13.0 mmol). The suspension is stirred at RT for 3 h then is poured into water and extracted with EtOAc. The organic layer is washed with water and brine, and dried over sodium sulfate. The solvent is removed under reduced pressure and the residue purified by flash chromatography eluting with hexanes/EtOAc (5:1 to 1:1) to afford the title compound as a colorless liquid: 1H NMR (CDCl3) δ 7.38-7.19 (m, 6H), 6.57-6.51 (dd, J=8.34, 12.63 Hz, 2H), 5.10 (s, 1H), 4.60 (s, 1H), 4.00 (t, J=6.06 Hz, 2H), 3.88 (s, 3H), 3.18-3.13 (m, 2H), 1.81-1.75 (m, 2H), 1.66-1.59 (m, 2H), 1.43 (s, 9H).

Provenance & Evidence