Ethyl Acetate → HCID 87329412, compound

Participants

Reaction Steps

To a solution of 4-aminooxymethyl-benzoic acid, hydrochloride 111 (2.0 g, 0.010 mol) in dioxane (20 mL) and half saturated Na2CO3 solution (20 mL) was added Fmoc-Cl (2.8 g, 0.011 mol) and the mixture was stirred for 2 h. Ethyl acetate (100 mL) was added and the pH of the aqueous phase was adjusted to 1-3 by careful addition of HCl(conc.). The mixture was poured in to a separating funnel and the organic phase was isolated, washed once with water (100 mL), dried over Na2SO4 and the solvent was removed on a rotavap to give an oil that solidified upon standing. The crude product was purified by flash column chromatography (petroleum ether, ethyl acetate, AcOH 60:40:1). Yield: 3.5 g (92%) 1H-NMR (250 MHz, DMSO-d6) =4.05 (1H, t, J=6.3 Hz), 4.27 (2H, d, J=6.3 Hz), 4.51 (2H, s), 7.08-7.22 (6H, m), 7.46 (2H, d, J=7.4 Hz), 7.66 (2H, d, J=7.1 Hz), 7.72 (2H, d, J=8.4 Hz), 10.29 (1H, br. s), 12.78 (1H, br. s). 13C-NMR (63 MHz, DMSO-d6) =47.04, 66.03, 76.91, 120.51, 125.41, 127.45, 128.03, 128.89, 129.33, 129.63, 130.82, 141.19, 144.01, 157.12, 167.48. MS (ES) m/z=389 (MH+). 1The material was prepared as previously described: Deles, J. et al.; PJCHDQ; Pol. J. Chem.; EN; 53; 1979; 1025-1032

Provenance & Evidence