Ethanol → HCID 21841502, compound

HRID 1739572Notes

Reaction equation

HRID 1739572 reaction equation
[CH:1]([N:4]([CH:32]([CH3:34])[CH3:33])[C:5](=[O:31])[CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([NH:22][O:23]CC3C=CC=CC=3)=[O:21])=[CH:16][CH:15]=2)=[CH:10][CH:9]=1)([CH3:3])[CH3:2].C(O)C>[Pd].C(OCC)(=O)C>[CH:32]([N:4]([CH:1]([CH3:3])[CH3:2])[C:5](=[O:31])[CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([NH:22][OH:23])=[O:21])=[CH:16][CH:15]=2)=[CH:10][CH:9]=1)([CH3:34])[CH3:33]

Participants

5

Reactant 2

HCID 702EthanolHCID 21841482HCID 21841482, compound

Product 1

HCID 21841502HCID 21841502, compoundYield 8.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

80 mg of the benzyl hydroxamate of Stage A were mixed with 50 mg of palladium on charcoal, 5 ml of ethanol and 40 ml of ethyl acetate, and the mixture was stirred for 8 hours under a hydrogen atmosphere. The reaction medium was filtered and evaporated under reduced pressure. The residue was purified by chromatography on silica, eluting with a mixture of cyclohexane/ethyl acetate (50/50) then ethyl acetate and finally ethyl acetate/acetic acid 99/1. The product was finally crystallized from ethyl acetate to obtain 5.2 mg of the expected product.

Workup

  1. filtrationThe reaction medium was filtered
  2. customevaporated under reduced pressure
  3. customThe residue was purified by chromatography on silica
  4. washeluting with a mixture of cyclohexane/ethyl acetate (50/50)
  5. customThe product was finally crystallized from ethyl acetate

Sources & evidence

ORD record
ord-fd897327e82d4836a48126604286806c
Source dataset
uspto-grants-1999_10
Patent number
US05965763

Reaction notes

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