Thiazole → (2RS)-3-Hexadecyloxy-2-(5-phenyl-3-isoxazolyloxy)propyl 2-thiazolioethyl phosphate

HRID 974674Notes

Reaction equation

HRID 974674 reaction equation
[P:1]([O-:40])([O:36][CH2:37][CH2:38]Br)([O:3][CH2:4][CH:5]([O:24][C:25]1[CH:29]=[C:28]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[O:27][N:26]=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][CH3:23])=[O:2].[S:41]1[CH:45]=[CH:44][N:43]=[CH:42]1>C1(C)C=CC=CC=1>[P:1]([O-:40])([O:36][CH2:37][CH2:38][C:42]1[S:41][CH:45]=[CH:44][NH+:43]=1)([O:3][CH2:4][CH:5]([O:24][C:25]1[CH:29]=[C:28]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[O:27][N:26]=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][CH3:23])=[O:2]

Participants

4

Reactant 2

HCID 9256ThiazoleHCID 19986049HCID 19986049, compound

Product 1

HCID 67869606(2RS)-3-Hexadecyloxy-2-(5-phenyl-3-isoxazolyloxy)propyl 2-thiazolioethyl phosphate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 0.925 g of the crude (2RS)-3-hexadecyloxy-2-(5-phenyl-3-isoxazolyloxy)propyl 2-bromoethyl phosphate obtained as described in the first part of Example 7 and 0.51 ml of thiazole in 0.8 ml of toluene was heated on an oil bath kept at 70° C. for 5 days, whilst stirring. The mixture was then cooled and freed from toluene by evaporation under reduced pressure. 15 ml of chloroform were then added to the residue, followed by 0.296 g of silver carbonate. The mixture was then heated under reflux for 1 hour. At the end of this time, the mixture was cooled, an insoluble material was filtered off and the solvent was stripped off from the filtrate by evaporation under reduced pressure. The residue was subjected to column chromatography through 20 g of silica gel. 0.117 g of the title compound was obtained as a viscous oil from the fractions eluted with a 1:1 by volume mixture of methanol and methylene chloride and with a 35:60:5 by volume mixture of methanol, methylene chloride and water.

Workup

  1. customobtained
  2. temperaturewas heated on an oil bath
  3. temperatureThe mixture was then cooled
  4. customfreed from toluene by evaporation under reduced pressure
  5. addition15 ml of chloroform were then added to the residue
  6. temperatureThe mixture was then heated
  7. temperatureunder reflux for 1 hour
  8. temperatureAt the end of this time, the mixture was cooled
  9. filtrationan insoluble material was filtered off
  10. customthe solvent was stripped off from the filtrate by evaporation under reduced pressure

Sources & evidence

ORD record
ord-05860f71ed4d4fce9b1b4834b40b6828
Source dataset
uspto-grants-1991_11
Patent number
US05068340

Reaction notes

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