HCID 44609103, compound → (R)-N-Hydroxy-3-(4-hydroxy-phenyl)-2-[(3-methyl-butyl)-(naphthalene-2-sulfonyl)-amino]-propionamide

Participants

Reaction Steps

A mixture of (R)-3-(4-benzyloxy-phenyl)-N-hydroxy-2-[(3-methyl-butyl)-(naphthalene-2-sulfonyl)-amino]-propionamide (230 mg, 0.42 mmol) and 200 mg of 10% Pd/C in ethyl acetate (20 mL) are hydrogenated under 50 PSI for 6 h. The reaction mixture is filtered through celite, and concentrated in vacuo. Purification by flash chromatography yields 40 mg of product. 1HNMR (400 MHz, MeOD): δ 0.90 (d, 6H, J=5.5 Hz), 1.5-1.7 (m, 4H), 2.4-2.5 (dd, 1H, J=5 Hz), 3.05-3.15 (dd, 1H, J=5 Hz), 3.35-3.45 (m, 1H), 3.6-3.75 (m, 1H), 4.30-4.40 (q, 1H, J=5 Hz), 6.55 (d, 2H, J=8 Hz), 6.80 (d, 2H, J=8 Hz), 7.7-7.85 (m, 3H), 7.92-8.10 (m, 3H), 8.45 (s, 1H). LCMS (m/z): 457 (M+1). Analytics calculated for C24H28N2O54S: C, 63.14; H, 6.18; N, 6.14. Found: C, 63.03; H, 6.30; N, 5.89.

Provenance & Evidence