HCID 19389152, compound → HCID 19389059, compound

HRID 1757852Notes

Reaction equation

HRID 1757852 reaction equation
C1(C[O:8][C:9](=[O:59])[CH2:10][N:11]([CH2:48][C:49](=[O:58])[O:50]CC2C=CC=CC=2)[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[C:14]([O: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][CH3:47])[CH:13]=2)C=CC=CC=1.[H][H]>[Pd].C1COCC1.C(OCC)(=O)C>[C:9]([CH2:10][N:11]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[C:14]([O: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][CH3:47])[CH:13]=1)[CH2:48][C:49]([OH:58])=[O:50])([OH:59])=[O:8]

Participants

6

Reactant 2

HCID 19389152HCID 19389152, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19389059HCID 19389059, compoundYield 56%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-[2-oxo-2-(phenylmethoxy)ethyl]-N-[3,4-bis(tetradecyloxy)phenyl]glycine phenylmethyl ester and 0.5 g of 10% palladium on carbon in 40 ml of THF and 20 ml of ethyl acetate was stirred in a hydrogen atmosphere at room temperature for 2.5 hours when uptake ceased. The catalyst was removed by filtration and the filtrate was concentrated at reduced pressure to a solid which was triturated with hexane and filtered to give 1.4 g (56% yield, mp 89°-93°) of pure N-(carboxymethyl)-N-[3,4-bis(tetradecyloxy)phenyl]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 hexane
  4. filtrationfiltered

Sources & evidence

ORD record
ord-42ded5a36ba94c13ba4dc84dd79177cf
Source dataset
uspto-grants-1995_08
Patent number
US05446189

Reaction notes

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