Niacin sodium → (R)-(2-pentadecanoyloxy-3-tridecyloxycarbonylpropyl)trimethylammonium nicotinate

HRID 1599519Notes

Reaction equation

HRID 1599519 reaction equation
[Cl-].[C:2]([O:18][C@H:19]([CH2:25][C:26]([O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])=[O:27])[CH2:20][N+:21]([CH3:24])([CH3:23])[CH3:22])(=[O:17])[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].[C:42]([O-:50])(=[O:49])[C:43]1[CH:48]=[CH:47][CH:46]=[N:45][CH:44]=1.[Na+]>O>[C:42]([O-:50])(=[O:49])[C:43]1[CH:48]=[CH:47][CH:46]=[N:45][CH:44]=1.[C:2]([O:18][C@H:19]([CH2:25][C:26]([O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])=[O:27])[CH2:20][N+:21]([CH3:22])([CH3:23])[CH3:24])(=[O:17])[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

4

Reactant 2

HCID 23687810Niacin sodiumHCID 86752438HCID 86752438, compound

Product 1

HCID 67643542(R)-(2-pentadecanoyloxy-3-tridecyloxycarbonylpropyl)trimethylammonium nicotinateYield 94.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of (R)-(2-pentadecanoyloxy-3-tridecyloxycarbonylpropyl)trimethylammonium chloride (1.5 g, 2.48 mmol) obtained in Example 2 and sodium nicotinate (3.0 g, 20.7 mmol) in 30 ml of tetrahydrofuran-ethyl acetate (1:1) was added 15 ml of water, and the mixture was stirred for 46.5 hours at room temperature. After the organic layer was separated and washed with 10 ml of water, the solvent was removed under reduced pressure, and the residue was azeotroped with ethyl acetate. The residual oily product was dissolved in 20 ml of diethyl ether, and the insoluble materials were removed by filtration. After diethyl ether was removed under reduced pressure, the residue was dried to give 1.62 g of (R)-(2-pentadecanoyloxy-3-tridecyloxycarbonylpropyl)trimethylammonium nicotinate as a colorless solid.

Workup

  1. customAfter the organic layer was separated
  2. washwashed with 10 ml of water
  3. customthe solvent was removed under reduced pressure
  4. customthe residue was azeotroped with ethyl acetate
  5. dissolutionThe residual oily product was dissolved in 20 ml of diethyl ether
  6. customthe insoluble materials were removed by filtration
  7. customAfter diethyl ether was removed under reduced pressure
  8. customthe residue was dried

Sources & evidence

ORD record
ord-0d89327e2d1e4c22b9a6f3293390c519
Source dataset
uspto-grants-1998_04
Patent number
US05741816

Reaction notes

Loading…