HCID 59253955, compound → 6-[4-(6-Hydroxyhexanoylamino)phenoxy]hexanoic acid methyl ester

HRID 638756Notes

Reaction equation

HRID 638756 reaction equation
[CH3:1][O:2][C:3](=[O:32])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:31])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][O:23]CC2C=CC=CC=2)=[CH:12][CH:11]=1>CO.[Pd]>[CH3:1][O:2][C:3](=[O:32])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:11]=[CH:12][C:13]([NH:16][C:17](=[O:31])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][OH:23])=[CH:14][CH:15]=1

Participants

4

Reactant 1

HCID 59253955HCID 59253955, compound

Product 1

HCID 592539566-[4-(6-Hydroxyhexanoylamino)phenoxy]hexanoic acid methyl esterYield 62.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

6-[4-(6-Benzyloxyhexanoylamino)phenoxy]hexanoic acid methyl ester 80 (10 g, 22.67 mmol) was dissolved in methanol (100 ml) in a pressure vessel, palladium on carbon (5%, 6 grams) added, and the mixture stirred under a hydrogen atm. (4 Kg) for 20 hrs. Catalyst was removed by filtration and methanol distilled off. Crude 81 was purified by column chromatography on silica gel using chloroform as eluant to give pure 81 (5 g, 62.8%) as a white powder. M.p: 73-75.5°

Workup

  1. customCatalyst was removed by filtration and methanol
  2. distillationdistilled off
  3. customCrude 81 was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-b9f54e85a39345b6aad9ee367be9e6c1
Source dataset
uspto-grants-2010_04
Patent number
US07691364B2

Reaction notes

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