Benzoyl chloride → 3-[2-(Benzoylamino-methyl)4-hydroxy-phenyl]propionic acid tert-butyl ester

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Reaction Steps

A slurry of 3-(2-aminomethyl-4-hydroxy-phenyl)-propionic acid tert-butyl ester (0.36 g, 1.43 mmol) in CH2Cl2 (10 mL) was cooled in an ice-water bath and treated with triethyl amine (0.40 mL, 0.28 mmol) then dropwise with benzoyl chloride (0.18 mL, 1.55 mmol). The resulting solution was stirred 30 min, and the cooling bath was removed. After 30 min, the solution was concentrated, and the residue was partitioned between EtOAc (50 mL) and 1N HCl (10 mL). The organic layer was washed with brine (10 mL), dried (Na2SO4), and concentrated to a solid. The crude mixture was purified by radial chromatography (hexanes:EtOAc 3:1 to 2:1) to give the title compound as a white solid (325 mg, 64%): 1H NMR (400 MHz, CDCl3) 1.26 (s, 9H), 2.54 (t, J=7.1 Hz, 2H), 2.81 (t, J=6.8 Hz, 2H), 4.55 (d, J=2H), 6.68 (dd, J=8.3, 2.4 Hz, 1H), 6.86 (d, J=2.9 Hz, 1H), 6.96 (d, J=8.3 Hz, 1H), 7.25-7.29 (m, 2H), 7.34-7.37 (m, 1H), 7.49 (br s, 1H), 7.16-7.79 (m, 2H); MS (ES) m/z 356.2 (M+H).

Provenance & Evidence