N-[3,5-bis(decyloxy)phenyl]-N-[2-oxo-2-(phenylmethoxy)ethyl]glycine phenylmethyl ester → N-(carboxymethyl)-N-(3,5-bis(decyloxy)-phenyl)glycine

HRID 1757778Notes

Reaction equation

HRID 1757778 reaction equation
C1(C[O:8][C:9](=[O:51])[CH2:10][N:11]([C:23]2[CH:28]=[C:27]([O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[CH:26]=[C:25]([O:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])[CH:24]=2)[CH2:12][C:13](=[O:22])[O:14]CC2C=CC=CC=2)C=CC=CC=1.[H][H]>[Pd]>[C:9]([CH2:10][N:11]([C:23]1[CH:28]=[C:27]([O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[CH:26]=[C:25]([O:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])[CH:24]=1)[CH2:12][C:13]([OH:22])=[O:14])([OH:51])=[O:8]

Participants

4

Reactant 2

HCID 10032668N-[3,5-bis(decyloxy)phenyl]-N-[2-oxo-2-(phenylmethoxy)ethyl]glycine phenylmethyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 192621N-(carboxymethyl)-N-(3,5-bis(decyloxy)-phenyl)glycineYield 75%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of 10.2 g (0.0145 mol) of N-[3,5-bis(decyloxy)phenyl]-N-[2-oxo-2-(phenylmethoxy)ethyl]glycine phenylmethyl ester and 1.5 g of 10% palladium on charcoal in 500 ml of THFwas shaken in a hydrogen atmosphere at room temperature for 7 hours. The catalyst was removed by filtration and the filtrate was concentrated underreduced pressure to a solid which was recrystallized from acetonitrile to give 5.66 g (75% yield, mp 110°-114°) of N-(carboxymethyl)-N-[3,5-bis(decyloxy)phenyl]glycine.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated underreduced pressure to a solid which
  3. customwas recrystallized from acetonitrile

Sources & evidence

ORD record
ord-512e75dd8f6845bcae723c4d6fe6721c
Source dataset
uspto-grants-1995_08
Patent number
US05446189

Reaction notes

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