N-benzyloxy-4-[3-(4-dimethylamino-benzyl)-ureido]-butyramide → 4-[3-(4-Dimethylamino-benzyl)-ureido]-N-hydroxy-butyramide
Reaction equation
C([O:8][NH:9][C:10](=[O:28])[CH2:11][CH2:12][CH2:13][NH:14][C:15]([NH:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]([CH3:27])[CH3:26])=[CH:21][CH:20]=1)=[O:16])C1C=CC=CC=1>CO.[Pd]>[CH3:27][N:25]([CH3:26])[C:22]1[CH:21]=[CH:20][C:19]([CH2:18][NH:17][C:15](=[O:16])[NH:14][CH2:13][CH2:12][CH2:11][C:10]([NH:9][OH:8])=[O:28])=[CH:24][CH:23]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of the N-benzyloxy-4-[3-(4-dimethylamino-benzyl)-ureido]-butyramide (287 mg, 0.747 mmol) in methanol (15 mL) was added 10% palladium on carbon (30 mg) and the resulting reaction was allowed to stir under a hydrogen atmosphere for 18 hr, after which time the reaction mixture was filtered and concentrated in vacuo to provide provide compound 2, which was used without further purification. (203 mg, 92% yield). 1H NMR (300 MHz, DMSO-d6) δ (ppm) 10.38 (s, 1H), 8.69 (s, 1H), 7.06 (d, J=9.0 Hz, 2H), 6.67(d, J=9.0 Hz, 2H), 6.10 (t, J=5.4 Hz, 1H), 5.87 (t, J=5.4 Hz, 1H), 4.06 (d, J=5.7 Hz, 2H), 2.97 (dt, J=6.6, 6.3 Hz, 2H), 2.85 (s, 6H), 1.94 (t, J=7.2 Hz, 2H), 1.57 (m, 2H). 13C NMR (75 MHz, DMSO-d6) δ (ppm) 168.8, 157.9, 149.4, 128.2, 127.9, 112.3, 42.4, 40.2, 38.8, 29.8, 26.3.