HCID 72551665, compound → HCID 15982715, compound

HRID 749026Notes

Reaction equation

HRID 749026 reaction equation
[CH3:1][N:2]([CH3:42])[C:3](=[O:41])[CH:4]([NH:30][S:31]([C:34]1[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][CH:35]=1)(=[O:33])=[O:32])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][C:20](=[O:29])[NH:21][O:22]C3C=CC=CC=3)=[CH:14][CH:13]=2)=[CH:8][CH:7]=1.[H][H]>CO.[Pd]>[OH:22][NH:21][C:20]([CH2:19][CH2:18][C:15]1[CH:16]=[CH:17][C:12]([C:9]2[CH:10]=[CH:11][C:6]([CH2:5][CH:4]([NH:30][S:31]([C:34]3[CH:35]=[CH:36][C:37]([CH3:40])=[CH:38][CH:39]=3)(=[O:33])=[O:32])[C:3]([N:2]([CH3:42])[CH3:1])=[O:41])=[CH:7][CH:8]=2)=[CH:13][CH:14]=1)=[O:29]

Participants

5

Reactant 2

HCID 72551665HCID 72551665, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15982715HCID 15982715, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Palladium (5% on BaSO4) (0.5 g) was added to a degassed solution of the benzyl hydroxamate 56 (0.8 g) in MeOH (50 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 57 (0.2 g, 29%). 1H NMR (400 MHz, DMSO-d6): 10.39 (br, 1H), 8.09 (d, J=9.6 Hz, 1H), 7.54 (d, J=8.4 Hz, 2H), 7.49 (d, J=8.4 Hz, 2H), 7.27 (d, J=8.4 Hz, 2H), 7.24 (d, J=8.4 Hz, 2H), 7.18 (d, J=8.4 Hz, 2H), 4.33 (m, 1H), 2.81-2.86 (m, 3H), 2.75 (s, 3H), 2.61-2.67 (m, 1H), 2.53 (s, 3H), 2.28 (s, 3H).

Workup

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

Sources & evidence

ORD record
ord-a690f7b0330c4baea5f713f59fafaddf
Source dataset
uspto-grants-2008_07
Patent number
US07399786B2

Reaction notes

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