Triethylamine → HCID 86752436, compound

HRID 1599518Notes

Reaction equation

HRID 1599518 reaction equation
C(N(CC)CC)C.[Br:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].[Cl-].[C:23]([CH2:26][C@@H:27]([O:33][C:34](=[O:47])[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])[CH2:28][N+:29]([CH3:32])([CH3:31])[CH3:30])([OH:25])=[O:24]>CN(C)C=O>[Br-:8].[C:34]([O:33][C@H:27]([CH2:26][C:23]([O:25][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH3:9])=[O:24])[CH2:28][N+:29]([CH3:30])([CH3:31])[CH3:32])(=[O:47])[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 130001-BromotridecaneHCID 86752437HCID 86752437, compound

Product 1

HCID 86752436HCID 86752436, compoundYield 105.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Triethylamine (0.53 ml, 3.81 mmol) and 1-bromotridecane (5.0 g, 19.0 mmol) were added successively to a suspension of (R)-(3-carboxy-2-tridecanoyloxypropyl)trimethylammonium chloride (1.5 g, 3.81 mmol) in 30 ml of dimethylformamide, and the mixture was stirred for 23 hours at 50° to 60° C. under argon atmosphere. The solvent of the reaction mixture was removed under reduced pressure. To the residue was added 20 ml of diethyl ether, and the mixture was stirred at room temperature. Thereafter, the precipitates were collected by filtration, washed with diethyl ether, and dried to give 2.5 g of crude (R)-(2-tridecanoyloxy-3-tridecyloxycarbonylpropyl)trimethylammonium bromide as a colorless solid. To 2.5 g of the product thus obtained was added 50 ml of water, and the mixture was stirred for 1 hour at room temperature and then extracted with tetrahydrofuran-ethyl acetate (1:1). To the extracted organic layer were added 100 ml of a saturated saline solution and 30 ml of water, and the mixture was stirred for 18 hours at room temperature. Thereafter, the organic layer was collected, washed with a saturated saline solution and then water, and the solvent was removed under reduced pressure. The residue was azeotroped with ethyl acetate and then dried at room temperature under reduced pressure to afford 1.75 g of a crude desired product. The product obtained was recrystallized from ethyl acetate to provide 1.58 g of (R)-(2-tridecanoyloxy-3-tridecyloxycarbonylpropyl)trimethylammonium chloride as colorless crystals.

Workup

  1. customThe solvent of the reaction mixture was removed under reduced pressure
  2. additionTo the residue was added 20 ml of diethyl ether
  3. stirringthe mixture was stirred at room temperature
  4. filtrationThereafter, the precipitates were collected by filtration
  5. washwashed with diethyl ether
  6. customdried

Sources & evidence

ORD record
ord-17422aa0ef2246f880aab7f158e9897a
Source dataset
uspto-grants-1998_04
Patent number
US05741816

Reaction notes

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