(2-{4-[4-(2-Benzyloxycarbamoylethyl)-phenoxy]-phenyl}-1-dimethylcarbamoyl-ethyl)-carbamic acid tert-butyl ester → (1-Dimethylcarbamoyl-2-{4-[4-(2-hydroxycarbamoyl-ethyl)-phenoxy]-phenyl}-ethyl)-carbamic acid tert-butyl ester

HRID 748980Notes

Reaction equation

HRID 748980 reaction equation
[C:1]([O:5][C:6](=[O:41])[NH:7][CH:8]([C:36](=[O:40])[N:37]([CH3:39])[CH3:38])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][C:25](=[O:35])[NH:26][O:27]CC3C=CC=CC=3)=[CH:19][CH:18]=2)=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[Pd]>[C:1]([O:5][C:6](=[O:41])[NH:7][CH:8]([C:36](=[O:40])[N:37]([CH3:39])[CH3:38])[CH2:9][C:10]1[CH:11]=[CH:12][C:13]([O:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][C:25](=[O:35])[NH:26][OH:27])=[CH:19][CH:18]=2)=[CH:14][CH:15]=1)([CH3:2])([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 59762819(2-{4-[4-(2-Benzyloxycarbamoylethyl)-phenoxy]-phenyl}-1-dimethylcarbamoyl-ethyl)-carbamic acid tert-butyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 59762805(1-Dimethylcarbamoyl-2-{4-[4-(2-hydroxycarbamoyl-ethyl)-phenoxy]-phenyl}-ethyl)-carbamic acid tert-butyl esterYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Palladium on BaSO4 (5%, 4.0 g) was added to a degassed solution of the benzyl hydroxamate 7 (4.6 g) in MeOH (200 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 8 (3.5 g, 93%). 1H NMR (DMSO-d6): 10.37 (s, 1H), 8.71 (s, 1H), 7.24 (d, J=8.4 Hz, 2H), 7.18 (d, J=8.4 Hz, 2H), 7.07 (d, J=8.4 Hz, 1H), 6.89 (d, J=8.4 Hz, 2H), 6.86 (d, J=8.8 Hz, 2H), 4.54 (ddd, J=14.8, 8.8, and 6.0 Hz, 1H), 2.91 (s, 3H), 2.70-2.87 (m, 7H), 2.24 (t, J=7.2 Hz, 2H), 1.32 (s, 9H).

Workup

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

Sources & evidence

ORD record
ord-0b539da6387a4572a337293dd9105c8b
Source dataset
uspto-grants-2008_07
Patent number
US07399786B2

Reaction notes

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