HCID 19389110, compound → HCID 19389136, compound

HRID 1757868Notes

Reaction equation

HRID 1757868 reaction equation
[C:1]([CH2:4][N:5]([C:10]1[CH:15]=[C:14]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([O:28]CC3C=CC=CC=3)[C:23]=2[O:36]CC2C=CC=CC=2)[CH:13]=[C:12]([O:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH3:62])[CH:11]=1)[CH2:6][C:7]([OH:9])=[O:8])([OH:3])=[O:2]>[Pd].O1CCCC1>[C:7]([CH2:6][N:5]([C:10]1[CH:11]=[C:12]([O:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH3:62])[CH:13]=[C:14]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([OH:28])[C:23]=2[OH:36])[CH:15]=1)[CH2:4][C:1]([OH:3])=[O:2])([OH:9])=[O:8]

Participants

4

Reactant 1

HCID 19389110HCID 19389110, compound

Product 1

HCID 19389136HCID 19389136, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 0.918 g of N-(carboxymethyl)-N-[3-(octadecyloxy)-5-[5-[2,3-bis(phenylmethoxy)phenyl]pentoxy]phenyl]glycine and 0.3 g of 10% palladium on carbon in 50 ml of tetrahydrofuran was stirred under a hydrogen atmosphere for 4 hours when absorption ceased. The catalyst was removed by filtration through a Celitepad and the filtrate was concentrated to a solid which was triturated with hexane and filtered to give 0.653 g (92% yield, mp 129°-131°) of N-(carboxymethyl)-N-[3-[5-(2,3-dihydroxyphenyl)pentoxy]-5-(octadecyloxy)phenyl]glycine.

Workup

  1. customwhen absorption
  2. customThe catalyst was removed by filtration through a Celitepad
  3. concentrationthe filtrate was concentrated to a solid which
  4. customwas triturated with hexane
  5. filtrationfiltered

Sources & evidence

ORD record
ord-2634867b3863485385ea25eaa45dbc6c
Source dataset
uspto-grants-1995_08
Patent number
US05446189

Reaction notes

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