Triethylamine → 3-(4-Chlorobutylsulfonylamino)-2-methoxy-1-octadecylcarbamoyloxypropane

HRID 728428

Reaction equation

HRID 728428 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].C(N(CC)CC)C.[Cl:36][CH2:37][CH2:38][CH2:39][CH2:40][S:41](Cl)(=[O:43])=[O:42]>ClCCl>[Cl:36][CH2:37][CH2:38][CH2:39][CH2:40][S:41]([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:43])=[O:42]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 742124-Chlorobutane-1-sulphonyl chlorideHCID 149922622-Methoxy-3-octadecylcarbamoyloxypropylamine

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of 1.2 g (3 mM) of 2-methoxy-3-octadecylcarbamoyloxypropylamine IVa1 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 IIIa5 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-3eaddd452a6a4961beaa3b84ccbf49b8
Source dataset
uspto-grants-1991_09
Patent number
US05047540

Linked notes

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