2-[4-(2-Benzyloxyacetylamino)phenoxy]propionic acid methyl ester → 2-[4-(2-Hydroxyacetylamino)phenoxy]propionic acid methyl ester

HRID 83816Notes

Reaction equation

HRID 83816 reaction equation
[CH3:1][O:2][C:3](=[O:25])[CH:4]([O:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:24])[CH2:15][O:16]CC2C=CC=CC=2)=[CH:9][CH:8]=1)[CH3:5]>CO.[Pd]>[CH3:1][O:2][C:3](=[O:25])[CH:4]([O:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:24])[CH2:15][OH:16])=[CH:9][CH:8]=1)[CH3:5]

Participants

4

Reactant 1

HCID 592539632-[4-(2-Benzyloxyacetylamino)phenoxy]propionic acid methyl ester

Product 1

HCID 592539602-[4-(2-Hydroxyacetylamino)phenoxy]propionic acid methyl esterYield 36.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-[4-(2-Benzyloxyacetylamino)-phenoxy]-propionic acid methyl ester 51 (15 gm, 43.7 mmol) was dissolved in methanol (150 ml) in a pressure vessel. Palladium on carbon (5%, 8 g) was added and the mixture stirred under a hydrogen atmosphere (2.5 kg) for 10 hrs. Catalyst was removed by filtration and the methanol distilled off. The crude 52 was recrystallised in chloroform:hexane (1:6) to give pure 52 (4 g, 36.3%) as a white powder with an m.p. between 111-112.6° C. IH NMR (CDCl3) δ 1.60 (d, 3H, CH3), 3.44 (bt, 1H, OH), 3.78 (s, 3H, Ester), 4.14 (d, 1H, CH2OH), 4.72 (q, 1H, CH), 6.80 (d, 2H, Ar), 7.44 (d, 2H, Ar), 8.30 (s, 1H, NH)

Workup

  1. customCatalyst was removed by filtration
  2. distillationthe methanol distilled off
  3. customThe crude 52 was recrystallised in chloroform:hexane (1:6)

Sources & evidence

ORD record
ord-18b99d1a9e294853ad43a470ac19b3b7
Source dataset
uspto-grants-2014_09
Patent number
US08846845B2

Reaction notes

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