N-(carboxymethyl)-N-[3-(octadecyloxy)-5-(phenylmethoxy)benzoyl]glycine → N-(carboxymethyl)-N-[3-hydroxy-5-(octadecyloxy)benzoyl]glycine

HRID 488271Notes

Reaction equation

HRID 488271 reaction equation
[C:1]([CH2:4][N:5]([C:10](=[O:44])[C:11]1[CH:16]=[C:15]([O:17]CC2C=CC=CC=2)[CH:14]=[C:13]([O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[CH:12]=1)[CH2:6][C:7]([OH:9])=[O:8])([OH:3])=[O:2].[H][H]>[Pd].C1COCC1>[C:7]([CH2:6][N:5]([C:10](=[O:44])[C:11]1[CH:12]=[C:13]([O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[CH:14]=[C:15]([OH:17])[CH:16]=1)[CH2:4][C:1]([OH:3])=[O:2])([OH:9])=[O:8]

Participants

5

Reactant 2

HCID 19091809N-(carboxymethyl)-N-[3-(octadecyloxy)-5-(phenylmethoxy)benzoyl]glycineHCID 178418361HCID 178418361, compound

Product 1

HCID 19091766N-(carboxymethyl)-N-[3-hydroxy-5-(octadecyloxy)benzoyl]glycine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 0.30 g of N-(carboxymethyl)-N-[3-(octadecyloxy)-5-(phenylmethoxy)benzoyl]glycine and 0.1 g of 10% palladium on carbon in 25 ml of THF was stirred in a hydrogen atmosphere for 2 hours. The usual workup followed by recrystallization from ether-hexane gave N-(carboxymethyl)-N-[3-hydroxy-5-(octadecyloxy)benzoyl]glycine, mp 160°-164°.

Workup

  1. customThe usual workup followed by recrystallization from ether-hexane

Sources & evidence

ORD record
ord-d90564ba45fc48a6a5ba4a46872d34a3
Source dataset
uspto-grants-1994_03
Patent number
US05298652

Reaction notes

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