HCID 72551669, compound → HCID 72551663, compound

HRID 749033Notes

Reaction equation

HRID 749033 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][CH:20]=[CH:19][C:18]=2[CH2:23][CH2:24][C:25](=[O:35])[NH:26][O:27]CC2C=CC=CC=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][CH:20]=[CH:19][C:18]=2[CH2:23][CH2:24][C:25](=[O:35])[NH:26][OH:27])=[CH:14][CH:15]=1)([CH3:2])([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 72551669HCID 72551669, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 72551663HCID 72551663, compoundYield 119.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Palladium on BaSO4 (5%, 0.24 g) was added to a degassed solution of the benzyl hydroxamate 63 (0.7 g) in MeOH (20.0 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 64 (0.7 g, 97%). 1H NMR (DMSO-d6): 10.37 (s, 1H), 7.28 (d, J=7.6 Hz, 1H), 7.23-7.16 (m, 3H), 7.06 (t, J=8.4 Hz, 2H), 6.85 (d, J=8.8 Hz, 2H), 6.76 (d, J=7.6 Hz, 1H), 4.53 (m, 1H), 2.80 (s, 3H), 2.79-2.75 (m, 7H), 2.23 (t, J=2.0 Hz, 2H), 1.30 (s, 9H).

Workup

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

Sources & evidence

ORD record
ord-89876c6e147043a2a7631e4f81faae04
Source dataset
uspto-grants-2008_07
Patent number
US07399786B2

Reaction notes

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