Sodium Iodide → HCID 19018990, compound

HRID 1757843Notes

Reaction equation

HRID 1757843 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 70.2%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.0 g (1.92 mmol) 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 wasconcentrated and crystallized from methylene chloride-methanol to give 0.99g (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. customcrystallized from methylene chloride-methanol

Sources & evidence

ORD record
ord-66f035c8b545439db8398d0d0f4a0ecb
Source dataset
uspto-grants-1995_08
Patent number
US05446189

Reaction notes

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