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

HRID 83820Notes

Reaction equation

HRID 83820 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 atmos-phere (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-c01af6c225694f85a1ba115dce5f7d20
Source dataset
uspto-grants-2014_09
Patent number
US08846845B2

Reaction notes

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