HCID 19389160, compound → N-(2-methoxy-2-oxoethyl)-N-[3-hydroxy-5-(octadecyloxy)phenyl]glycine methyl ester

HRID 1110285Notes

Reaction equation

HRID 1110285 reaction equation
[CH3:1][O:2][C:3](=[O:44])[CH2:4][N:5]([CH2:39][C:40]([O:42][CH3:43])=[O:41])[C:6]1[CH:11]=[C:10]([O:12]CC2C=CC=CC=2)[CH:9]=[C:8]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[CH:7]=1.[H][H]>[Pd].C1COCC1>[CH3:1][O:2][C:3](=[O:44])[CH2:4][N:5]([C:6]1[CH:7]=[C:8]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[CH:9]=[C:10]([OH:12])[CH:11]=1)[CH2:39][C:40]([O:42][CH3:43])=[O:41]

Participants

5

Reactant 2

HCID 19389160HCID 19389160, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19388979N-(2-methoxy-2-oxoethyl)-N-[3-hydroxy-5-(octadecyloxy)phenyl]glycine methyl esterYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 15.55 g of N-(2-methoxy-2-oxoethyl)-N-[3-(octadecyloxy)-5-(phenylmethoxy)phenyl]glycine methyl ester and 3.0 g of 10% palladium on carbon in 500 ml of THF was stirred in a hydrogen atmosphere at room temperature until uptake ceased after 23 hours. 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 12.8 g (97% yield, 96°-98°) of N-[3-hydroxy-5-(octadecyloxy)phenyl]-N-(2-methoxy-2-oxoethyl)glycine methyl ester.

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-d85d507635304863a40680385fc38f3f
Source dataset
uspto-grants-1994_06
Patent number
US05324747

Reaction notes

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