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

HRID 1786734Notes

Reaction equation

HRID 1786734 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 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
  4. customto provide
  5. customprovide compound 2,which
  6. customwas used without further purification

Sources & evidence

ORD record
ord-00df31b315224b0db81c5d1232c5d610
Source dataset
uspto-grants-2009_03
Patent number
US07507828B2

Reaction notes

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