HCID 72575118, compound → HCID 72575123, compound

HRID 273431Notes

Reaction equation

HRID 273431 reaction equation
C([O:8][C:9](=[O:44])[CH:10]([NH:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19]2[CH:24]=[CH:23][C:22]([C:25](=[O:35])[NH:26][O:27]CC3C=CC=CC=3)=[CH:21][CH:20]=2)=[CH:14][CH:13]=1)C1C=CC=CC=1.[H][H]>[Pd].CO>[C:40]([O:39][C:37]([NH:36][CH:10]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19]2[CH:24]=[CH:23][C:22]([C:25](=[O:35])[NH:26][OH:27])=[CH:21][CH:20]=2)=[CH:14][CH:13]=1)[C:9]([OH:44])=[O:8])=[O:38])([CH3:43])([CH3:41])[CH3:42]

Participants

5

Reactant 2

HCID 72575118HCID 72575118, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 72575123HCID 72575123, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Palladium on carbon (5%, 0.3 g) was added to a degassed solution of the benzyl hydroxamate 7 (0.4 g) in MeOH (25 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 8 (0.2 g, 72%). 1H NMR (DMSO-d6): 11.20 (s, 1H), 9.02 (br, 1H), 7.75 (d, J=8.8 Hz, 2H), 7.30 (d, J=8.8 Hz, 2H), 7.11 (d, J=8.8 Hz, 1H), 6.99 (d, J=8.8 Hz, 2H), 6.96 (d, J=8.8 Hz, 2H), 4.10 (ddd, J=12.8 10.0, and 4.4 Hz, 1H), 3.03 (dd, J=13.6 and 4.4 Hz, 1H), 2.82 (dd, J=13.6 and 10.4 Hz, 1H), 1.33 (s, 9H).

Workup

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

Sources & evidence

ORD record
ord-1621211990ba4716a08eee7fb9fa5ee1
Source dataset
uspto-grants-2008_11
Patent number
US07456292B2

Reaction notes

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