Pyridine → HCID 67780521, compound

HRID 2248048Notes

Reaction equation

HRID 2248048 reaction equation
ClC([O:4][C:5]1C=CC=CC=1)=O.[OH:11][CH2:12][CH2:13][CH2:14][NH:15][C:16]([O:18][CH2:19][CH:20]([CH2:23][O:24][C:25](=[O:34])[NH:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1)[O:21][CH3:22])=[O:17].[N:35]1C=CC=CC=1.[CH2:41](N)[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH3:58]>C(Cl)Cl>[CH3:22][O:21][CH:20]([CH2:23][O:24][C:25](=[O:34])[NH:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1)[CH2:19][O:18][C:16](=[O:17])[NH:15][CH2:14][CH2:13][CH2:12][O:11][C:5](=[O:4])[NH:35][CH:43]([CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH3:58])[CH2:42][CH3:41]

Participants

6

Reactant 4

HCID 1049PyridineHCID 15793OctadecylamineHCID 15891Phenyl chloroformateHCID 67780457HCID 67780457, compound

Product 1

HCID 67780521HCID 67780521, compoundYield 55.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.56 g of phenyl chloroformate was added dropwise to 50 ml of a solution of 2.9 g of 1-O-(3-hydroxy)propylcarbamoyl-2-O-methyl-3-O-(2-pyridyl)methylcarbamoylglycerol and 1.3 g of pyridine in methylene chloride under cooling with ice and the mixture was stirred for 15 min. The reaction solution was washed with a saturated aqueous solution of sodium hydrogen-carbonate and then with water and dried over anhydrous magnesium sulfate. The solvent was removed and a residue thus formed was mixed with 3 g of octadecylamine. The mixture was stirred at 80° C. for 1 h. After cooling, the product was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/1) to obtain 3 g of the intended product.

Workup

  1. temperatureunder cooling with ice
  2. washThe reaction solution was washed with a saturated aqueous solution of sodium hydrogen-carbonate
  3. dry with materialwith water and dried over anhydrous magnesium sulfate
  4. customThe solvent was removed
  5. customa residue thus formed
  6. stirringThe mixture was stirred at 80° C. for 1 h
  7. temperatureAfter cooling
  8. customthe product was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/1)

Sources & evidence

ORD record
ord-d2164c39fd814944899ed930f89fb351
Source dataset
uspto-grants-1991_08
Patent number
US05037827

Reaction notes

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