Thiazole → HCID 67903130, compound

HRID 846967Notes

Reaction equation

HRID 846967 reaction equation
[CH2:1]([O:17][CH2:18][CH:19]([O:29][CH3:30])[CH2:20][NH:21][S:22]([CH2:25][CH2:26][CH2:27][I:28])(=[O:24])=[O:23])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[S:31]1[CH:35]=[CH:34][N:33]=[CH:32]1>>[I-:28].[CH2:1]([O:17][CH2:18][CH:19]([O:29][CH3:30])[CH2:20][NH:21][S:22]([CH2:25][CH2:26][CH2:27][C:32]1[S:31][CH:35]=[CH:34][NH+:33]=1)(=[O:24])=[O:23])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

3

Reactant 2

HCID 9256ThiazoleHCID 14835025HCID 14835025, compound

Product 1

HCID 67903130HCID 67903130, compoundYield 66%

Procedure

A solution of 600 mg (1.07 mM) of 1-hexadecyloxy-3-(3-iodopropylsulfonylamino)-2-methoxypropane in 5 ml of thiazole is stirred at 50° C. for 6 hours. After thiazole is evaporated, the residue is purified by the column chromatography on silica gel with a chloroform-methanol (5:1 to 3:1) mixture as an eluent. The product is recrystallized from ether-dichloromethane to give 450 mg (0.70 mM) of 1-hexadecyloxy-2-methoxy-3-(3-thiazoliopropylsulfonylamino)propane iodide I a11 in 66% yield.

Workup

  1. customAfter thiazole is evaporated
  2. customthe residue is purified by the column chromatography on silica gel with a chloroform-methanol (5:1 to 3:1) mixture as an eluent
  3. customThe product is recrystallized from ether-dichloromethane

Sources & evidence

ORD record
ord-69b962745b27402ab28063398db13524
Source dataset
uspto-grants-1992_08
Patent number
US05138067

Reaction notes

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