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

Participants

Reaction Steps

Palladium on BaSO4 (5%, 4.0 g) was added to a degassed solution of the benzyl hydroxamate 7 (4.6 g) in MeOH (200 mL) and the suspension was treated with hydrogen at atmospheric pressure for 6 h. The suspension was filtered over a Celite® bed and concentrated to yield the desired hydroxamate 8 (3.5 g, 93%). 1H NMR (DMSO-d6): 10.37 (s, 1H), 8.71 (s, 1H), 7.24 (d, J=8.4 Hz, 2H), 7.18 (d, J=8.4 Hz, 2H), 7.07 (d, J=8.4 Hz, 1H), 6.89 (d, J=8.4 Hz, 2H), 6.86 (d, J=8.8 Hz, 2H), 4.54 (ddd, J=14.8, 8.8, and 6.0 Hz, 1H), 2.91 (s, 3H), 2.70-2.87 (m, 7H), 2.24 (t, J=7.2 Hz, 2H), 1.32 (s, 9H).

Provenance & Evidence