4-Chlorobutane-1-sulphonyl chloride → 3-(4-Chlorobutylsulfonylamino)-2-methoxy-1-octadecylcarbamoyloxypropane

HRID 846969Notes

Reaction equation

HRID 846969 reaction equation
[CH3:1][O:2][CH:3]([CH2:6][O:7][C:8](=[O:28])[NH:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:4][NH2:5].[Cl:29][CH2:30][CH2:31][CH2:32][CH2:33][S:34](Cl)(=[O:36])=[O:35]>ClCCl.C(N(CC)CC)C>[Cl:29][CH2:30][CH2:31][CH2:32][CH2:33][S:34]([NH:5][CH2:4][CH:3]([O:2][CH3:1])[CH2:6][O:7][C:8](=[O:28])[NH:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])(=[O:36])=[O:35]

Participants

5

Reactant 2

HCID 742124-Chlorobutane-1-sulphonyl chlorideHCID 149922622-Methoxy-3-octadecylcarbamoyloxypropylamine

Product 1

HCID 148350313-(4-Chlorobutylsulfonylamino)-2-methoxy-1-octadecylcarbamoyloxypropaneYield 77%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent3×HCID 8471TriethylamineSolvent

Procedure

To a solution of 1.2 g (3 mM) of 2-methoxy-3-octadecylcarbamoyloxypropylamine IV a1 in 24 ml of dichloromethane and 0.5 ml (3.6 mM) of triethylamine is added 0.75 g (3.93 mM) of 4-chlorobutanesulfonyl chloride with ice-cooling and the mixture is stirred at room temperature overnight. The product is isolated with dichloromethane extraction and dichloromethane layer is washed with saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and evaporated. The residue is purified by the column chromatography on silica gel with a n-hexane-ethyl acetate (3:2) mixture as an eluent. The product is recrystallized from dichloromethane-n-hexane to give 1.28 g (2.305 mM) of 3-(4-chlorobutylsulfonylamino)-2-methoxy-1-octadecylcarbamoyloxypropane III a5 as colorless crystals in 77% yield.

Workup

  1. temperaturecooling
  2. washis washed with saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated
  5. customThe residue is purified by the column chromatography on silica gel with a n-hexane-ethyl acetate (3:2) mixture as an eluent
  6. customThe product is recrystallized from dichloromethane-n-hexane

Sources & evidence

ORD record
ord-088f8902b7234dad98272f57e5e0ac2b
Source dataset
uspto-grants-1992_08
Patent number
US05138067

Reaction notes

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