Thiazole → 2-Methoxy-1-octadecylcarbamoyloxy-3-(4-thiazoliobutylsulfonylamino)propane iodide

HRID 728430Notes

Reaction equation

HRID 728430 reaction equation
[I:1][CH2:2][CH2:3][CH2:4][CH2:5][S:6]([NH:9][CH2:10][CH:11]([O:35][CH3:36])[CH2:12][O:13][C:14](=[O:34])[NH: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][CH2:30][CH2:31][CH2:32][CH3:33])(=[O:8])=[O:7].[S:37]1[CH:41]=[CH:40][N:39]=[CH:38]1>>[I-:1].[CH3:36][O:35][CH:11]([CH2:10][NH:9][S:6]([CH2:5][CH2:4][CH2:3][CH2:2][C:38]1[S:37][CH:41]=[CH:40][NH+:39]=1)(=[O:8])=[O:7])[CH2:12][O:13][C:14](=[O:34])[NH: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][CH2:30][CH2:31][CH2:32][CH3:33]

Participants

3

Reactant 2

HCID 9256ThiazoleHCID 148350323-(4-Iodobutylsulfonylamino)-2-methoxy-1-octadecylcarbamoyloxypropane

Product 1

HCID 679029612-Methoxy-1-octadecylcarbamoyloxy-3-(4-thiazoliobutylsulfonylamino)propane iodideYield 41%

Procedure

A solution of 300 mg (0.464 mM) of 3-(4-iodobutylsulfonylamino)-2-methoxy-1-octadecylcarbamoyloxypropane in 3 ml of thiazole is stirred at 60° C. for 6 hours. After thiazole is evaporated, the residue is washed with ether and recrystallized from ether-dichloromethane to give 140 mg (0.191 mM) of 2-methoxy-1-octadecylcarbamoyloxy-3-(4-thiazoliobutylsulfonylamino)propane iodide Ia13 in 41% yield.

Workup

  1. customAfter thiazole is evaporated
  2. washthe residue is washed with ether
  3. customrecrystallized from ether-dichloromethane

Sources & evidence

ORD record
ord-2825e95a5fa148ed9bec32a2bcbb0eed
Source dataset
uspto-grants-1991_09
Patent number
US05047540

Reaction notes

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