Nicotinic Acid → HCID 53842741, compound

HRID 414705Notes

Reaction equation

HRID 414705 reaction equation
[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.O1CCCC1.C1(N=C=NC2CCCCC2)CCCCC1.[C:30]([NH:51][CH2:52][CH2:53]O)(=[O:50])[CH2:31][CH2:32][CH2:33][CH:34]=[CH:35][CH2:36][CH:37]=[CH:38][CH2:39][CH:40]=[CH:41][CH2:42][CH:43]=[CH:44][CH2:45][CH:46]=[CH:47][CH2:48][CH3:49]>CN(C)C1C=CN=CC=1.ClCCCl>[C:1]([O:9][CH2:53][CH2:52][NH:51][C:30](=[O:50])[CH2:31][CH2:32][CH2:33][CH:34]=[CH:35][CH2:36][CH:37]=[CH:38][CH2:39][CH:40]=[CH:41][CH2:42][CH:43]=[CH:44][CH2:45][CH:46]=[CH:47][CH2:48][CH3:49])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1

Participants

7

Reactant 4

HCID 938Nicotinic AcidHCID 8028TetrahydrofuranHCID 10868DicyclohexylcarbodiimideHCID 54171584HCID 54171584, compound

Product 1

HCID 53842741HCID 53842741, compoundYield 96.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 111,2-DichloroethaneSolvent2×

Procedure

To a solution of 77 mg (0.63 mmol) of nicotinic acid in a mixed solvent of tetrahydrofuran (2 ml) and 1,2-dichloroethane (2 ml) at room temperature were successively added in an atmosphere of argon 7 mg (0.06 mmol) of 4-dimethylaminopyridine, 129 mg (0.63 mmol) of N,N'-dicyclohexylcarbodiimide and 196 mg (0.57 mmol) of N-5,8,11,14,17-eicosapentaenoyl-2-aminoethanol, which were dissolved in 1,2-dichloroethane (1.5 ml), respectively. The mixture was reacted overnight, and precipitates then produced were separated by filtration and washed with benzene. To the mother liquor was added water, and the mixture was extracted three times with dichloromethane. The organic layer from the extraction was washed with water and dried over anhydrous sodium sulfate. The solvent was then removed by distillation under reduced pressure to give 311 mg of extraction residue, which was subjected to silica gel column chromatography. From a fraction eluted with chloroform-methanol (98:2) was obtained 246 mg (0.55 mmol) of N-(5,8,11,14,17-eicosapentaenoyl)-2-aminoethyl nicotinate. Physicochemical properties of the product supports the formula (III) shown below.

Workup

  1. customThe mixture was reacted overnight
  2. customprecipitates
  3. customthen produced
  4. customwere separated by filtration
  5. washwashed with benzene
  6. additionTo the mother liquor was added water
  7. extractionthe mixture was extracted three times with dichloromethane
  8. extractionThe organic layer from the extraction
  9. washwas washed with water
  10. dry with materialdried over anhydrous sodium sulfate
  11. customThe solvent was then removed by distillation under reduced pressure
  12. customto give
  13. extraction311 mg of extraction residue, which
  14. washFrom a fraction eluted with chloroform-methanol (98:2)

Sources & evidence

ORD record
ord-a7545c8861a446c4aa279020a8f89a35
Source dataset
uspto-grants-1988_12
Patent number
US04794115

Reaction notes

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