({4-[4-(2-Benzoyloxycarbamoylethyl)-phenoxy]-phenyl}-dimethylcarbamoylmethyl)-carbamic acid tert-butyl ester → (Dimethylcarbamoyl-{4-[4-(2-hydroxycarbamoyl-ethyl)-phenoxy]-phenyl}-methyl)-carbamic acid tert-butyl ester

HRID 749006Notes

Reaction equation

HRID 749006 reaction equation
[C:1]([O:5][C:6](=[O:41])[NH:7][CH:8]([C:14]1[CH:19]=[CH:18][C:17]([O:20][C:21]2[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][C:29](=[O:40])[NH:30][O:31]C(=O)C3C=CC=CC=3)=[CH:23][CH:22]=2)=[CH:16][CH:15]=1)[C:9](=[O:13])[N:10]([CH3:12])[CH3:11])([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[Pd]>[C:1]([O:5][C:6](=[O:41])[NH:7][CH:8]([C:9](=[O:13])[N:10]([CH3:12])[CH3:11])[C:14]1[CH:15]=[CH:16][C:17]([O:20][C:21]2[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][C:29](=[O:40])[NH:30][OH:31])=[CH:23][CH:22]=2)=[CH:18][CH:19]=1)([CH3:2])([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 59751124({4-[4-(2-Benzoyloxycarbamoylethyl)-phenoxy]-phenyl}-dimethylcarbamoylmethyl)-carbamic acid tert-butyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 59751091(Dimethylcarbamoyl-{4-[4-(2-hydroxycarbamoyl-ethyl)-phenoxy]-phenyl}-methyl)-carbamic acid tert-butyl esterYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Palladium (5% on BaSO4, 2.0 g) was added to a degassed solution of the benzyl hydroxamate 34 (1.5 g) in MeOH (100 mL) and the suspension was treated with hydrogen at atmospheric pressure for 6 h. The suspension was filtered over a Celite® bed and concentrated to yield the desired hydroxamate 35 (1.1 g, 90%). 1H NMR (400 MHz, DMSO-d6): 10.42 (s, 1H), 7.33 (d, J=8.4 Hz, 2H), 7.22 (d, J=8.4 Hz, 2H), 7.12 (d, J=8.4 Hz, 1H), 6.93 (overlapped d, J=8.8 Hz, 2H), 6.92 (overlapped d, J=8.4 Hz, 2H), 5.50 (d, J=8.0 Hz, 1H), 2.90 (s, 3H), 2.84 (s, 3H), 2.80 (t, J=8.0 Hz, 2H), 2.25 (t, J=7.6 Hz, 2H), 1.37 (s, 9H).

Workup

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

Sources & evidence

ORD record
ord-7249142ed092467b98fffc9451d0aac1
Source dataset
uspto-grants-2008_07
Patent number
US07399786B2

Reaction notes

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