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

HRID 501869Notes

Reaction equation

HRID 501869 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 61 (10 g, 22.67 mmol) was dissolved in methanol (100 ml) in a pressure vessel. Palladium on carbon (5%, 6 grm) was added and the mixture stirred under a hydrogen atmosphere (4 kg) for 20 hrs. The catalyst was removed by filtration, and methanol distilled off. Crude 62 was purified by column chromatography on silica gel using chloroform as eluant to give pure 62 (5 g, 62.8%) as a white powder with a m.p. between 73-75.5° C.

Workup

  1. customThe catalyst was removed by filtration, and methanol
  2. distillationdistilled off
  3. customCrude 62 was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-292e16187f924a95b9a0a705b3ed5f3e
Source dataset
uspto-grants-2010_08
Patent number
US07772352B2

Reaction notes

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