3-{4-[4-(2-benzyloxycarbamoylethyl)-phenoxy]-phenyl}-N,N-dimethyl-2-(toluene-4-sulfonylamino)-propionamide → 3-{4-[4-(2-hydroxycarbamoyl-ethyl)-phenoxy]-phenyl}-N,N-dimethyl-2-(toluene-4-sulfonylamino)-propionamide

HRID 748999Notes

Reaction equation

HRID 748999 reaction equation
C([O:8][NH:9][C:10]([CH2:12][CH2:13][C:14]1[CH:44]=[CH:43][C:17]([O:18][C:19]2[CH:24]=[CH:23][C:22]([CH2:25][CH:26]([NH:32][S:33]([C:36]3[CH:41]=[CH:40][C:39]([CH3:42])=[CH:38][CH:37]=3)(=[O:35])=[O:34])[C:27]([N:29]([CH3:31])[CH3:30])=[O:28])=[CH:21][CH:20]=2)=[CH:16][CH:15]=1)=[O:11])C1C=CC=CC=1.[H][H]>CO.[Pd]>[OH:8][NH:9][C:10]([CH2:12][CH2:13][C:14]1[CH:15]=[CH:16][C:17]([O:18][C:19]2[CH:20]=[CH:21][C:22]([CH2:25][CH:26]([NH:32][S:33]([C:36]3[CH:37]=[CH:38][C:39]([CH3:42])=[CH:40][CH:41]=3)(=[O:35])=[O:34])[C:27]([N:29]([CH3:31])[CH3:30])=[O:28])=[CH:23][CH:24]=2)=[CH:43][CH:44]=1)=[O:11]

Participants

5

Reactant 2

HCID 724251493-{4-[4-(2-benzyloxycarbamoylethyl)-phenoxy]-phenyl}-N,N-dimethyl-2-(toluene-4-sulfonylamino)-propionamideHCID 178418361HCID 178418361, compound

Product 1

HCID 159825793-{4-[4-(2-hydroxycarbamoyl-ethyl)-phenoxy]-phenyl}-N,N-dimethyl-2-(toluene-4-sulfonylamino)-propionamideYield 59%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Palladium on BaSO4 (5%, 0.5 g) was added to a degassed solution of the benzyl hydroxamate 26 (0.8 g) in MeOH (50 mL) and the suspension was treated with hydrogen at atmospheric pressure for 4 h. The suspension was filtered over a Celite® bed and concentrated to yield the desired hydroxamate 27 (0.4 g, 59%). 1H NMR (400 MHz, DMSO-d6): 10.36 (s, 1H), 8.70 (br, 1H), 8.05 (d, J=9.2 Hz, 1H), 7.54 (d, J=8.4 Hz, 2H), 7.29 (d, J=7.6 Hz, 2H), 7.19 (d, J=8.8 Hz, 2H), 7.10 (d, J=8.4 Hz, 2H), 6.86 (d, J=8.8 Hz, 2H), 6.82 (d, J=8.8 Hz, 2H), 4.29 (m, 1H), 2.73-2.80 (m, 3H), 2.67 (s, 3H), 2.59 (dd, J=13.2 and 7.6 Hz, 1H), 2.99 (s, 3H), 2.24 (t, J=8.0 Hz, 2H). LCMS (m/e): Obsd. 511, Calcd. 510.6

Workup

  1. filtrationThe suspension was filtered over a Celite® bed
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-48e407f0f95a43379fafa3b6cb24acef
Source dataset
uspto-grants-2008_07
Patent number
US07399786B2

Reaction notes

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