6-[4-(2-Benzyloxyacetylamino)phenoxy]hexanoic acid methyl ester → HCID 59253948, compound

HRID 501866Notes

Reaction equation

HRID 501866 reaction equation
[CH3:1][O:2][C:3](=[O:28])[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:27])[CH2:18][O:19]CC2C=CC=CC=2)=[CH:12][CH:11]=1>CO.[Pd]>[CH3:1][O:2][C:3](=[O:28])[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:27])[CH2:18][OH:19])=[CH:14][CH:15]=1

Participants

4

Reactant 1

HCID 592539816-[4-(2-Benzyloxyacetylamino)phenoxy]hexanoic acid methyl ester

Product 1

HCID 59253948HCID 59253948, compoundYield 65.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

6-[4-(2-Benzyloxyacetylamino)-phenoxy]-hexanoic acid methyl ester 53 (1 grams, 2.6 mmol) was dissolved in methanol (10 ml) in a pressure vessel. Palladium on carbon (5%, 250 mg) was added and the mixture stirred under a hydrogen atmosphere (2 kg) for 5 hrs. Catalyst was removed by filtration and methanol distilled off. Crude 54 was recrystallised in chloroform:hexane (1:6) to get pure 54 (0.5 g, 65.3%) as a white powder with an m.p. between 91.5-94° C.

Workup

  1. customCatalyst was removed by filtration and methanol
  2. distillationdistilled off
  3. customCrude 54 was recrystallised in chloroform:hexane (1:6)

Sources & evidence

ORD record
ord-fa290c4f4b48461ba348a3d9f60e70e1
Source dataset
uspto-grants-2010_08
Patent number
US07772352B2

Reaction notes

Loading…