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

HRID 728419Notes

Reaction equation

HRID 728419 reaction equation
[I:1][CH2:2][CH2:3][CH2:4][S:5]([NH:8][CH2:9][CH:10]([O:34][CH3:35])[CH2:11][O:12][C:13](=[O:33])[NH: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][CH2:30][CH2:31][CH3:32])(=[O:7])=[O:6].[S:36]1[CH:40]=[CH:39][N:38]=[CH:37]1>>[I-:1].[CH3:35][O:34][CH:10]([CH2:9][NH:8][S:5]([CH2:4][CH2:3][CH2:2][C:37]1[S:36][CH:40]=[CH:39][NH+:38]=1)(=[O:7])=[O:6])[CH2:11][O:12][C:13](=[O:33])[NH: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][CH2:30][CH2:31][CH3:32]

Participants

3

Reactant 2

HCID 9256ThiazoleHCID 148350213-(3-Iodopropylsulfonylamino)-2-methoxy-1-octadecylcarbamoyloxypropane

Product 1

HCID 679030472-Methoxy-1-octadecylcarbamoyloxy-3-(3-thiazoliopropylsulfonylamino)propane iodideYield 55%

Procedure

A solution of 240 mg (0.38 mM) of 3-(3-iodopropylsulfonylamino)-2-methoxy-1-octadecylcarbamoyloxypropane in 2 ml of thiazole is stirred at 50° C. overnight. After thiazole is evaporated, the residue is recrystallized from dichloromethane-acetone to give 150 mg (0.209 mM) of 2-methoxy-1-octadecylcarbamoyloxy-3-(3-thiazoliopropylsulfonylamino)propane iodide Ia2 in 55% yield.

Workup

  1. customAfter thiazole is evaporated
  2. customthe residue is recrystallized from dichloromethane-acetone

Sources & evidence

ORD record
ord-29263ebcc0e9469e884479efde3a4f2c
Source dataset
uspto-grants-1991_09
Patent number
US05047540

Reaction notes

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