Triethylamine → (2-{4-[4-(2-Benzyloxycarbamoylethyl)-phenoxy]-phenyl}-1-dimethylcarbamoyl-ethyl)-carbamic acid tert-butyl ester

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Reaction Conditions

Reaction Steps

The acid compound 6 (4.8 g, 10.5 mmol) was dissolved in dry DMF and cooled to 0-5° C. 1-Hydroxybenzotriazole (1.56 g, 11.5 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI, 2.0 g, 10.5 mmol), and triethylamine (4.4 mL, 31.6 mmol) were added to the above mixture followed by stirring for 15 min. O-Benzylhydroxylamine hydrochloride (1.85 g, 11.5 mmol) was added and the mixture was allowed to come to room temperature and stirred for 18 h. The solvent was evaporated under reduced pressure and the residual oil was taken up in EtOAc (100 mL). The organic layer was extracted with 2.0 M HCl (1×20 mL), saturated NaHCO3 (1×20 mL), and brine (1×50 mL). The resulting EtOAc layer was dried and concentrated to yield the crude product. Flash chromatography (30-70% ethyl acetate in hexane containing 1% acetic acid) yielded the desired benzyl hydroxamate 7 (4.7 g, 78%). 1H NMR (400 MHz, DMSO-d6): 10.96 (s, 1H), 7.32-7.38 (m, 5H), 7.23 (d, J=8.8 Hz, 2H), 7.17 (d, J=8.4 Hz, 7.06 (d, J=8.0 Hz, 1H), 6.86 (overlapped d, J=8.4 Hz, 4H), 4.72 (s, 2H), 4.53 (m, 1H), 2.90 (s, 3H), 2.69-2.86 (m, 7H), 2.25 (t, J=7.6 Hz, 2H), 1.30 (s, 9H).

Provenance & Evidence