N-benzyloxy-4-[3-(4-dimethylamino-benzyl)-ureido]-butyramide → 4-[3-(4-Dimethylamino-benzyl)-ureido]-N-hydroxy-butyramide

HRID 404198Notes

Reaction equation

HRID 404198 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]=1

Participants

4

Reactant 1

HCID 86596090N-benzyloxy-4-[3-(4-dimethylamino-benzyl)-ureido]-butyramide

Product 1

HCID 575981614-[3-(4-Dimethylamino-benzyl)-ureido]-N-hydroxy-butyramideYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

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 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.

Workup

  1. customthe resulting reaction
  2. filtrationafter which time the reaction mixture was filtered
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b0c1f23398334ffeb8b7868924deb79c
Source dataset
uspto-grants-2014_06
Patent number
US08748463B2

Reaction notes

Loading…