Sodium Iodide → HCID 19018990, compound

HRID 1110287Notes

Reaction equation

HRID 1110287 reaction equation
[CH3:1][O:2][C:3](=[O:37])[CH2:4][N:5]([CH2:32][C:33]([O:35][CH3:36])=[O:34])[C:6]1[CH:11]=[C:10]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:9]=[C:8]([OH:31])[CH:7]=1.Br[CH2:39][CH2:40][CH2:41][O:42][C:43]1[CH:44]=[C:45]([Br:49])[CH:46]=[CH:47][CH:48]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CC(C)=O.CN(C=O)C>[CH3:1][O:2][C:3](=[O:37])[CH2:4][N:5]([CH2:32][C:33]([O:35][CH3:36])=[O:34])[C:6]1[CH:11]=[C:10]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:9]=[C:8]([O:31][CH2:39][CH2:40][CH2:41][O:42][C:43]2[CH:48]=[CH:47][CH:46]=[C:45]([Br:49])[CH:44]=2)[CH:7]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 19388979N-(2-methoxy-2-oxoethyl)-N-[3-hydroxy-5-(octadecyloxy)phenyl]glycine methyl esterHCID 193891331-Bromo-3-(3-bromopropoxy)benzene

Product 1

HCID 19018990HCID 19018990, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.0 g (1.92 mol) of N-(2-methoxy-2-oxoethyl)-N-[3-hydroxy-5-(octadecyloxy)phenyl]glycine methyl ester, 0.59 g (2.01 mmol) of 3-(3-bromopropoxy)bromobenzene, 0.53 g (3.83 mmol) of potassium carbonate and 0.29 g (1.92 mmol) of sodium iodide in 30 ml of acetone and 6 ml of DMF was stirred at reflux under argon for 65 hours. The solvents were removed at reduced pressure and the residue was treated with methylene chloride and filtered. The filtrate was concentrated and crystallized from methylene chloride-methanol to give 0.99 g (70%, mp 48°-50°) of N-(2-methoxy-2-oxoethyl)-N-[3-[3-(3-bromophenoxy)propoxy]-5-(octadecyloxy)phenyl]glycine methyl ester.

Workup

  1. temperatureat reflux under argon for 65 hours
  2. customThe solvents were removed at reduced pressure
  3. additionthe residue was treated with methylene chloride
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customcrystallized from methylene chloride-methanol

Sources & evidence

ORD record
ord-4b3c947dd98d442a9e857ad2f0bc3abd
Source dataset
uspto-grants-1994_06
Patent number
US05324747

Reaction notes

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