HCID 19388950, compound → HCID 19388999, compound

HRID 1110302Notes

Reaction equation

HRID 1110302 reaction equation
C1(C[O:8][C:9](=[O:53])[CH2:10][N:11]([C:23]2[CH:28]=[CH:27][C:26]([O:29][C:30](=[O:40])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])=[C:25]([O:41][C:42](=[O:52])[CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])[CH:24]=2)[CH2:12][C:13](=[O:22])[O:14]CC2C=CC=CC=2)C=CC=CC=1.[H][H]>[Pd].C(OCC)(=O)C.C1COCC1>[C:13]([CH2:12][N:11]([C:23]1[CH:28]=[CH:27][C:26]([O:29][C:30](=[O:40])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])=[C:25]([O:41][C:42](=[O:52])[CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])[CH:24]=1)[CH2:10][C:9]([OH:53])=[O:8])([OH:22])=[O:14]

Participants

6

Reactant 2

HCID 19388950HCID 19388950, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19388999HCID 19388999, compoundYield 78.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2.2 g of N-[3,4-bis[(1-oxodecyl)oxy]phenyl]-N-[2-oxo-2-(phenylmethoxy)ethyl]glycine phenylmethyl ester and 0.5 g of 10% palladium on carbon in 20 ml of ethyl acetate and 30 ml of THF was stirred in a hydrogen atmosphere at room temperature until uptake ceased after 10 hours. The catalyst was removed by filtration and the filtrate was concentrated at reduced pressure to a semisolid which was crystallized from ethyl acetate-hexane to give 1.3 g (78% yield, mp 131°-133°) of N-(carboxymethyl)-N-[3,4-bis[(1-oxodecyl)oxy]phenyl]glycine.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated at reduced pressure to a semisolid which
  3. customwas crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-166d47066ef14721be890d6a60d0d49f
Source dataset
uspto-grants-1994_06
Patent number
US05324747

Reaction notes

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