Pyridine → HCID 19986127, compound

HRID 974672Notes

Reaction equation

HRID 974672 reaction equation
[P:1]([O-:36])([O:32][CH2:33][CH2:34]Br)([O:3][CH2:4][CH:5]([O:26][C:27]1[CH:31]=[CH:30][O:29][N:28]=1)[CH2:6][O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[O:2].[N:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>>[P:1]([O-:36])([O:32][CH2:33][CH2:34][N+:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([O:3][CH2:4][CH:5]([O:26][C:27]1[CH:31]=[CH:30][O:29][N:28]=1)[CH2:6][O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[O:2]

Participants

3

Reactant 2

HCID 1049PyridineHCID 19986117HCID 19986117, compound

Product 1

HCID 19986127HCID 19986127, compound

Procedure

A solution of 0.663 g of crude (2RS)-3-octadecyloxy-2-(3-isoxazolyloxy)propyl 2-bromoethyl phosphate (prepared as described in the first part of Example 2) in 4.5 ml of pyridine was heated on an oil bath kept at 60° C. for 11 hours. After allowing the mixture to cool, excess pyridine was distilled off. The residue was dissolved in 10 ml of chloroform, and the solution was heated under reflux for 1 hour. The mixture was then cooled, and the solvent was evaporated off under reduced pressure. Methanol was then added to the residue, and the resulting insoluble material was filtered off. The filtrate was concentrated by evaporation under reduced pressure, and the residue was subjected to column chromatography through 15 g of silica gel. 0.305 g of the title compound was obtained as a hygroscopic powder, melting at 49°-52° C., from the fractions eluted with a 2:1 by volume mixture of methylene chloride and methanol.

Workup

  1. temperaturewas heated on an oil bath
  2. temperatureto cool
  3. distillationexcess pyridine was distilled off
  4. dissolutionThe residue was dissolved in 10 ml of chloroform
  5. temperaturethe solution was heated
  6. temperatureunder reflux for 1 hour
  7. temperatureThe mixture was then cooled
  8. customthe solvent was evaporated off under reduced pressure
  9. additionMethanol was then added to the residue
  10. filtrationthe resulting insoluble material was filtered off
  11. concentrationThe filtrate was concentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-7da28cb4881c4adea3da9d4380cabd70
Source dataset
uspto-grants-1991_11
Patent number
US05068340

Reaction notes

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