Sodium Iodide → HCID 19389016, compound

HRID 1757877Notes

Reaction equation

HRID 1757877 reaction equation
[CH3:1][O:2][C:3](=[O:37])[CH2:4][N:5]([C:11]1[CH:16]=[C:15]([O: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][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH:14]=[C:13]([OH:36])[CH:12]=1)[CH2:6][C:7]([O:9][CH3:10])=[O:8].Br[CH2:39][CH2:40][CH2:41][O:42][C:43]1[CH:48]=[CH:47][C:46]([S:49]([CH3:52])(=[O:51])=[O:50])=[CH:45][CH:44]=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]([CH2:6][C:7]([O:9][CH3:10])=[O:8])[C:11]1[CH:16]=[C:15]([O: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][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH:14]=[C:13]([O:36][CH2:39][CH2:40][CH2:41][O:42][C:43]2[CH:48]=[CH:47][C:46]([S:49]([CH3:52])(=[O:51])=[O:50])=[CH:45][CH:44]=2)[CH:12]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 15233479156450-83-8HCID 19388979N-(2-methoxy-2-oxoethyl)-N-[3-hydroxy-5-(octadecyloxy)phenyl]glycine methyl ester

Product 1

HCID 19389016HCID 19389016, compoundYield 73.1%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.0 g (1.92 mmol) of N-[3-hydroxy-5-(octadecyloxy)phenyl]-N-(2-methoxy-2-oxoethyl)glycine methyl ester, 0.84 g (2.88 mmol) of 1-(3-bromopropoxy)-4-(methylsulfonyl) benzene, 0.53 g (3.83 mmol) of potassium carbonate and 0.3 g (1.92 mmol) of sodium iodide in 30 ml of acetone and 6 ml of DMF was stirred at refluxunder argon for 72 hours. The solvents were removed at reduced pressure andthe residual oil was purified by three recrystallizations from methylene chloride-methanol to give 1.03 g (73% yield, mp 70°-72°) of N-(2-methoxy-2-oxoethyl)-N-[3-[3-[4-(methylsulfonyl)phenoxy]propoxy]-5-(octadecyloxy)-phenyl]glycine methyl ester.

Workup

  1. customfor 72 hours
  2. customThe solvents were removed at reduced pressure andthe residual oil
  3. customwas purified by three recrystallizations from methylene chloride-methanol

Sources & evidence

ORD record
ord-b177b8f245524714aaff9a19c8d0144d
Source dataset
uspto-grants-1995_08
Patent number
US05446189

Reaction notes

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