4-(2-Benzyloxyacetylamino)phenoxyacetic acid methyl ester → 4-(2-Hydroxyacetylamino)phenoxyacetic acid methyl ester

HRID 83814Notes

Reaction equation

HRID 83814 reaction equation
[CH3:1][O:2][C:3](=[O:24])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:23])[CH2:14][O:15]CC2C=CC=CC=2)=[CH:8][CH:7]=1>CO.[Pd]>[CH3:1][O:2][C:3](=[O:24])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:23])[CH2:14][OH:15])=[CH:8][CH:7]=1

Participants

4

Reactant 1

HCID 592539834-(2-Benzyloxyacetylamino)phenoxyacetic acid methyl ester

Product 1

HCID 592539714-(2-Hydroxyacetylamino)phenoxyacetic acid methyl esterYield 77%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

[4-(2-Benzyloxyacetylamino)phenoxy]acetic acid methyl ester 49 (25 g, 76 mmol) was dissolved in methanol (450 ml) in a pressure vessel. Palladium on carbon (5%, 10 g) 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 50 was recrystal-lised in chloroform:hexane (1:6) to give pure 50 (14 g) as a white powder with an m.p. between 147.5-150° C. IH NMR (CDCl3+DMSO-d6): δ 3.74 (s, 3H, ester), 3.96 (d, 2H, CH2OH), 4.64 (s, 2H, OCH2), 5.48 (t, 1H, OH), 6.80 (d, 2H, Ar), 7.54 (d, 2H, Ar) 9.2 (bs, 1H, NH)

Workup

  1. customCatalyst was removed by filtration and methanol
  2. distillationdistilled off

Sources & evidence

ORD record
ord-15aa536fd1674aaba150a110d931146b
Source dataset
uspto-grants-2014_09
Patent number
US08846845B2

Reaction notes

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