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

HRID 83821Notes

Reaction equation

HRID 83821 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-0b7bff0aaffd4e05ae39790fa3fd5402
Source dataset
uspto-grants-2014_09
Patent number
US08846845B2

Reaction notes

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