HCID 59762816, compound → HCID 59762809, compound

HRID 748993Notes

Reaction equation

HRID 748993 reaction equation
[C:1]([O:5][C:6](=[O:47])[NH:7][CH:8]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][C:28]2[CH:33]=[CH:32][C:31]([CH2:34][CH2:35][C:36](=[O:46])[NH:37][O:38]CC3C=CC=CC=3)=[CH:30][CH:29]=2)=[CH:23][CH:22]=1)[C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17](=[O:19])[CH3:18])[CH2:13][CH2:12]1)=[O:10])([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[Pd]>[C:1]([O:5][C:6](=[O:47])[NH:7][CH:8]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][C:28]2[CH:29]=[CH:30][C:31]([CH2:34][CH2:35][C:36](=[O:46])[NH:37][OH:38])=[CH:32][CH:33]=2)=[CH:23][CH:22]=1)[C:9]([N:11]1[CH2:12][CH2:13][N:14]([C:17](=[O:19])[CH3:18])[CH2:15][CH2:16]1)=[O:10])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 59762816HCID 59762816, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59762809HCID 59762809, compoundYield 103.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Palladium on BaSO4 (5%, 0.4 g) was added to a degassed solution of the benzyl hydroxamate 20 (0.9 g) in MeOH (75 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 21 (˜0.8 g, quantitative yield). 1H NMR (400 MHz, DMSO-d6): 10.38 (s, 1H), 8.72 (s, 1H), 7.24 (d, J=8.0 Hz, 2H), 7.16 (d, J=8.8 Hz, 2H), 6.88 (d, J=7.6 Hz, 2H), 6.83 (d, J=8.4 Hz, 2H), 4.58 (m, 1H) 3.10-3.45 (m, 8H), 2.76-2.85 (m, 4H), 2.24 (t, J=7.2 Hz, 2H), 2.00 (s, 3H), 1.32 (s, 9H).

Workup

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

Sources & evidence

ORD record
ord-3054b13c245d46a19cd23e6b861aeb97
Source dataset
uspto-grants-2008_07
Patent number
US07399786B2

Reaction notes

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