Hydrochloric Acid → HCID 23513882, compound

Participants

Reaction Steps

To methyl ({4-{[4-(2-butynyloxy)phenyl]sulfonyl}-4-[(hydroxyamino)carbonyl]-1-piperidinyl}methyl)benzoate hydrochloride (from example 77) (0.20 g) in methanol (10 mL) was added concentrated aqueous ammonium hydroxide (4 mL). After several weeks the reaction mixture was concentrated in vacuo and chromatographed on silica gel (methanol/dichloromethane) to give a white powder which was dissolved in dichloromethane and methanol. 1N Hydrochloric acid in diethylether was added followed by additional diethylether. Trituration gave 1-[4-(aminocarbonyl)benzyl]-4-{[4-(2-butynyloxy)phenyl]sulfonyl}-N-hydroxy-4-piperidinecarboxamide hydrochloride as a white powder (0.106 g). 1H NMR (Dmso d6, 300 MHz) δ1.85 (t, 3H, CH3, J=2.2 Hz), 2.2-3.5 (m, 8H, CH2), 4.33 (bd s, 2H, NCH2Ar), 4.89 (q, 2H, OCH2, J=2.2 Hz), 7.1-8.0 (m, 8H, ArH), 7.47 (s, CONH), 8.04 (s, 1H, CONH), 9.35 (bd s, 1H, NHOH), 10.44 (bd s, 1H, NHOH), 11.1 (s, 1H, NH). Electrospray MS m/z 486.3 (M+H)+

Provenance & Evidence