Ethanol → HCID 54420792, compound

HRID 1418152Notes

Reaction equation

HRID 1418152 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:13])[NH2:12])=[CH:7][C:6]=1[NH:14][C:15](=[O:39])[CH2:16][CH:17]([C:23]1[CH:28]=[CH:27][C:26]([O:29]CC2C=CC=CC=2)=[CH:25][C:24]=1[O:37][CH3:38])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])([CH3:4])(C)C.[H][H].[CH2:42](O)[CH3:43]>[Pd]>[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:13])[NH2:12])=[CH:7][C:6]=1[NH:14][C:15](=[O:39])[CH2:16][CH:17]([C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][C:24]=1[O:37][CH3:38])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:4][CH2:42][CH3:43]

Participants

5

Reactant 3

HCID 702EthanolHCID 19348468HCID 19348468, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 54420792HCID 54420792, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A solution of 2.46 g (4.64 mmol) of N-(2-t-butyl-5-carbamoylphenyl)-3-(4-benzyloxy-2-methoxyphenyl)octanamide (prepared as described in Example 123) in 100 ml of ethanol was vigorously stirred at 40° C. under a stream of hydrogen in the presence of 10% palladium-on-charcoal for 1.5 hours. At the end of this time, the reaction mixture was filtered using a Celite (trade mark) filter aid to remove the catalyst, and the filtrate was concentrated to dryness by evaporation under reduced pressure. The residue was purified by column chromatography through 100 g of silica gel using a 49:1 by volume mixture of ethyl acetate and methanol as the eluent, to give a crude product containing the title compound. This product was further purified by column chromatography through silica gel under the same conditions as above to give 1.62 g (yield 79%) of the title compound as a foam-like substance.

Workup

  1. filtrationAt the end of this time, the reaction mixture was filtered
  2. filtrationfilter aid
  3. customto remove the catalyst
  4. concentrationthe filtrate was concentrated to dryness by evaporation under reduced pressure
  5. customThe residue was purified by column chromatography through 100 g of silica gel using a 49:1
  6. additionby volume mixture of ethyl acetate and methanol as the eluent
  7. customto give a crude product

Sources & evidence

ORD record
ord-13a804488cf3476fb7742494e816a390
Source dataset
uspto-grants-1999_03
Patent number
US05880147

Reaction notes

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