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

HRID 501868Notes

Reaction equation

HRID 501868 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 59 (15 g, 37.59 mmol) was dissolved in methanol (150 ml) in a pressure vessel. Palladium on carbon (50% wet, 5%, 15 g) was added and the mixture stirred under hydrogen atmosphere (4 kg) for 16 hrs. Catalyst was removed by filtration and methanol distilled off. Crude 60 was purified by column chromatography on silica gel using chloroform as eluant to get pure 60 (6 g, 51.6%) as a white powder with an m.p between 62-64.5° C.

Workup

  1. customCatalyst was removed by filtration and methanol
  2. distillationdistilled off
  3. customCrude 60 was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-1d022c3a7d4d49fb95f89e168df0b6b8
Source dataset
uspto-grants-2010_08
Patent number
US07772352B2

Reaction notes

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