HCID 19091889, compound → HCID 19091807, compound

HRID 488292Notes

Reaction equation

HRID 488292 reaction equation
C1(C[O:8][C:9](=[O:58])[CH2:10][N:11]([C:23](=[O:57])[C:24]2[CH:29]=[C:28]([O: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][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48])[CH:27]=[CH:26][C:25]=2[O:49]CC2C=CC=CC=2)[CH2:12][C:13]([O:15]CC2C=CC=CC=2)=[O:14])C=CC=CC=1>[Pd].C1COCC1>[C:13]([CH2:12][N:11]([C:23](=[O:57])[C:24]1[CH:29]=[C:28]([O: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][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48])[CH:27]=[CH:26][C:25]=1[OH:49])[CH2:10][C:9]([OH:58])=[O:8])([OH:15])=[O:14]

Participants

4

Reactant 1

HCID 19091889HCID 19091889, compound

Product 1

HCID 19091807HCID 19091807, compoundYield 68.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 0.60 g of N-[5-(octadecyloxy)-2-(phenylmethoxy) benzoyl]-N-[2-(phenylmethoxy)-2-oxoethyl]glycine phenylmethyl ester and 0.20 g of 10% palladium on carbon in 20 ml of THF was stirred under a hydrogen atmosphere at room temperature for 23 hours. The catalyst was removed by filtration and the filtrate was concentrated at reduced pressure to a solid which was triturated with ether to give 0.27 g (68% yield, mp 128°-132°) of N-(carboxymethyl)-N-[2-hydroxy-5-(octadecyloxy)benzoyl]glycine.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated at reduced pressure to a solid which
  3. customwas triturated with ether

Sources & evidence

ORD record
ord-1b516a61c5b44a429d3f47478776ac0e
Source dataset
uspto-grants-1994_03
Patent number
US05298652

Reaction notes

Loading…