Sodium Iodide → Methyl 2-[(2-methoxy-2-oxoethyl)amino]acetate

HRID 1757886Notes

Reaction equation

HRID 1757886 reaction equation
[CH3:1][O:2][C:3](=[O:38])[CH2:4][N:5](C1C=C(OCCCCCCCCCCCCOC2C=CC=CC=2)C=C(O)C=1)[CH2:6][C:7]([O:9][CH3:10])=[O:8].BrCCCCCCC1C=CC=C(OCC2C=CC=CC=2)C=1OCC1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CC(C)=O.CN(C=O)C>[CH3:10][O:9][C:7](=[O:8])[CH2:6][NH:5][CH2:4][C:3]([O:2][CH3:1])=[O:38]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 149864341-(6-Bromohexyl)-2,3-bis(phenylmethoxy)benzeneHCID 19388995N-[3-hydroxy-5-[(12-phenoxydodecyl)oxy]phenyl]-N-(2-methoxy-2-oxoethyl)glycine methyl ester

Product 1

HCID 428827Methyl 2-[(2-methoxy-2-oxoethyl)amino]acetate

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.7 g (3.2 mmol) of N-[3-hydroxy-5-[(12-phenoxydodecyl)oxy]phenyl]-N-(2-methoxy-2-oxoethyl)glycine methyl ester, 1.5 g (3.37 mmol) of 1-(6-bromohexyl)-2,3-bis(phenylmethoxy)benzene, 1.3 g (9.6 mmol) of potassium carbonate and 0.96 g (6.4 mmol) of sodium iodide in 60 ml of acetone and 20 ml of DMF was stirred at reflux under argon for 7 days. Theusual workup followed by purification by HPLC using 25% ethyl acetate-hexane gave 2.15 g (74% yield) of N-[3-[6-(2,3-bisphenylmethoxy)phenyl]hexyloxy]-5-[(12-phenoxydodecyl)oxy]phenyl]-N-(2-methoxy-2-oxoethyl)glycine methyl ester as an oil. The nmr and mass spectra were consistent with the structure.

Workup

  1. temperatureat reflux under argon for 7 days
  2. customTheusual workup followed by purification by HPLC

Sources & evidence

ORD record
ord-1d78d97cffb348e4ab1daf5526c100d1
Source dataset
uspto-grants-1995_08
Patent number
US05446189

Reaction notes

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