HCID 59253980, compound → 2-[4-(6-Hydroxyhexanoylamino)phenoxy]propionic acid methyl ester

HRID 1957872Notes

Reaction equation

HRID 1957872 reaction equation
[CH3:1][O:2][C:3](=[O:29])[CH:4]([O:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:28])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][O:20]CC2C=CC=CC=2)=[CH:9][CH:8]=1)[CH3:5]>CO.[Pd]>[CH3:1][O:2][C:3](=[O:29])[CH:4]([O:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:28])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][OH:20])=[CH:9][CH:8]=1)[CH3:5]

Participants

4

Reactant 1

HCID 59253980HCID 59253980, compound

Product 1

HCID 592539432-[4-(6-Hydroxyhexanoylamino)phenoxy]propionic acid methyl esterYield 51.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-[4-(6-Benzyloxyhexanoylamino)phenoxy]propionic acid methyl ester 78 (15 g, 37.59 mmol) was dissolved in methanol (150 ml) in a pressure vessel, palladium on carbon (50% wet, 5%, 15 g) added and the mixture stirred under a hydrogen atmosph. (4 Kg) for 16 hrs. Catalyst was removed by filtration and methanol distilled off. The crude 79 was purified by column chromatography on silica gel using chloroform as eluant to get pure 79 (6 g, 51.6%) as a white powder. M.p: 62-64.5° C.

Workup

  1. customCatalyst was removed by filtration and methanol
  2. distillationdistilled off
  3. customThe crude 79 was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-6cd49050e6f4430f83d6887c11fd25e2
Source dataset
uspto-grants-2013_04
Patent number
US08409559B2

Reaction notes

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