Pyridine → HCID 67780521, compound

HRID 2260192Notes

Reaction equation

HRID 2260192 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 hydrogencarbonate 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 hydrogencarbonate
  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-d3793c362f9545b4926aaad15bfe70b3
Source dataset
uspto-grants-1995_12
Patent number
US05476863

Reaction notes

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