Sodium Iodide → N-(2-methoxy-2-oxoethyl)-N-[3-[(Z)-(9-octadecenyl)oxy]phenyl]glycine methyl ester

HRID 1110243Notes

Reaction equation

HRID 1110243 reaction equation
[CH3:1][O:2][C:3](=[O:18])[CH2:4][N:5]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([OH:17])[CH:12]=1)[CH2:6][C:7]([O:9][CH3:10])=[O:8].[CH2:19](Br)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]/[CH:27]=[CH:28]\[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36].[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.CN(C=O)C>[CH3:10][O:9][C:7](=[O:8])[CH2:6][N:5]([CH2:4][C:3]([O:2][CH3:1])=[O:18])[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]/[CH:27]=[CH:28]\[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH:12]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 58403839-Octadecene, 1-bromo-, (9Z)-HCID 193890473-hydroxyphenyl-N-(2-methoxy-2-oxoethyl)glycine methyl ester

Product 1

HCID 67788122N-(2-methoxy-2-oxoethyl)-N-[3-[(Z)-(9-octadecenyl)oxy]phenyl]glycine methyl esterYield 52.2%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.24 g (0.95 mmol) of N-(3-hydroxyphenyl)-N-(2-methoxy-2-oxoethyl)glycine methyl ester, 0.33 g (1 mmol) of oleyl bromide, 0.15 g (1 mmol) of sodium iodide and 0.41 g (3 mmol) of potassium carbonate in 10 ml of acetone was stirred at reflux under argon for 18 hours. DMF (5 ml) was added and reflux was continued for 3 days. The solvents were removed at reduced pressure and the residue was dissolved in ethyl acetate. The extract was dried and concentrated at reduced pressure to an oil which was purified by chromatography on 230-400 mesh silica gel using 25% ethyl acetate-hexane to give 0.25 g (50% yield, mp 36°-37°) of N-(2-methoxy-2-oxoethyl)-N-[3-[(Z)-(9-octadecenyl)oxy]phenyl]glycine methyl ester. The nmr and spectra were consistent with the structure.

Workup

  1. temperatureat reflux under argon for 18 hours
  2. temperaturereflux
  3. customThe solvents were removed at reduced pressure
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. customThe extract was dried
  6. concentrationconcentrated at reduced pressure to an oil which
  7. customwas purified by chromatography on 230-400 mesh silica gel using 25% ethyl acetate-hexane

Sources & evidence

ORD record
ord-af1b4db343824c7cb82bb8eafeefcc3f
Source dataset
uspto-grants-1994_06
Patent number
US05324747

Reaction notes

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