Thiazole → 2-Methoxy-1-octadecylcarbamoylthio-3-(3-thiazoliniopropylsulfonylamino)propane iodide

HRID 728435Notes

Reaction equation

HRID 728435 reaction equation
[I:1][CH2:2][CH2:3][CH2:4][S:5]([NH:8][CH2:9][CH:10]([O:34][CH3:35])[CH2:11][S: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][CH:37]1[NH+:38]=[CH:39][CH2:40][S:36]1)(=[O:7])=[O:6])[CH2:11][S: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 148350343-(3-Iodopropylsulfonylamino)-2-methoxy-1-octadecylcarbamoylthiopropane

Product 1

HCID 867450492-Methoxy-1-octadecylcarbamoylthio-3-(3-thiazoliniopropylsulfonylamino)propane iodideYield 37%

Procedure

A solution of 76 mg of 3-(3-iodopropylsulfonylamino)-2-methoxy-1-octadecylcarbamoylthiopropane IIa6 in 1 ml of thiazole is heated at 60° C. for 6 hours. After the solvent is evaporated, the residue is washed with ether and subsequently with acetonitrile to give 32 mg of 2-methoxy-1-octadecylcarbamoylthio-3-(3-thiazoliniopropylsulfonylamino)propane iodide Ia26 in 37% yield.

Workup

  1. customAfter the solvent is evaporated
  2. washthe residue is washed with ether and subsequently with acetonitrile

Sources & evidence

ORD record
ord-1137cbec9c5143e79b3afacebc64698c
Source dataset
uspto-grants-1991_09
Patent number
US05047540

Reaction notes

Loading…