HCID 72551666, compound → HCID 72551664, compound

HRID 749017Notes

Reaction equation

HRID 749017 reaction equation
[C:1]([O:5][C:6](=[O:39])[NH:7][CH:8]([C:34](=[O:38])[N:35]([CH3:37])[CH3:36])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][C:24](=[O:33])[NH:25][O:26]C3C=CC=CC=3)=[CH:18][CH:17]=2)=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[Pd]>[C:1]([O:5][C:6](=[O:39])[NH:7][CH:8]([C:34](=[O:38])[N:35]([CH3:37])[CH3:36])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][C:24](=[O:33])[NH:25][OH:26])=[CH:18][CH:17]=2)=[CH:12][CH:11]=1)([CH3:2])([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 72551666HCID 72551666, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 72551664HCID 72551664, compoundYield 97.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Palladium on BaSO4 (5%, 1.0 g) was added to a degassed solution of the benzyl hydroxamate 47 (1.2 g) in MeOH (60 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 48 (1.0 g, 97%). 1H NMR (DMSO-d6): 10.42 (br, 1H), 7.55 (d, J=7.6 Hz, 4H), 7.32 (d, J=8.0 Hz, 2H), 7.27 (d, J=8.4 Hz, 2H), 7.13 (d, J=8.4 Hz, 1H), 4.57 (m, 1H), 2.94 (s, 3H), 2.73-2.91 (m, 7H), 2.29 (t, J=8.0 Hz, 2H), 1.31 (s, 9H).

Workup

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

Sources & evidence

ORD record
ord-bc02cf3fc42d460ebba869f937f83abb
Source dataset
uspto-grants-2008_07
Patent number
US07399786B2

Reaction notes

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