Acetone → HCID 19986092, compound

HRID 974671Notes

Reaction equation

HRID 974671 reaction equation
[P:1]([O-:36])([O:32][CH2:33][CH2:34]Br)([O:3][CH2:4][CH:5]([O:26][C:27]1[S:28][CH:29]=[CH:30][N:31]=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].[CH3:37][N:38]([CH3:40])[CH3:39].C(=O)=O.CC(C)=O>C(Cl)(Cl)Cl.C(O)(C)C.CN(C)C=O.C(=O)([O-])[O-].[Ag+2]>[P:1]([O-:36])([O:32][CH2:33][CH2:34][N+:38]([CH3:40])([CH3:39])[CH3:37])([O:3][CH2:4][CH:5]([O:26][C:27]1[S:28][CH:29]=[CH:30][N:31]=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

9

Reactant 4

HCID 180AcetoneHCID 280Carbon DioxideHCID 1146TrimethylamineHCID 19986073HCID 19986073, compound

Product 1

HCID 19986092HCID 19986092, compound

Reagents, catalysts & solvents 4

HCID 178418647HCID 178418647, compoundCatalystHCID 3776IsopropanolSolventHCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

1(b) 1.056 g of the crude (2RS)-3-octadecyloxy-2-(2-thiazolyloxy)propyl 2-bromoethyl phosphate [prepared as described in step (a) above] was dissolved in 26 ml of a 3:5:5 by volume mixture of chloroform, isopropanol and dimethylformamide, and about 10 g of gaseous trimethylamine was introduced into the solution. The reaction mixture was then warmed, whilst stirring, for 5.5 hours on an oil bath kept at 50° C. in a reaction flask fitted with a reflux condenser cooled with dry ice and acetone. At the end of this time, the reaction mixture was cooled, and 0.355 g of silver carbonate was added. The mixture was then heated under reflux on an oil bath for 1 hour. The mixture was then cooled and concentrated by evaporation under reduced pressure. Methanol was added to the residue, and an insoluble material was filtered off. The solvent was stripped off from the filtrate, and the residue (1.07 g) was subjected to column chromatography through 25 g of silica gel. 0.690 g of the title compound was obtained as a white powder melting at 140° to 160° C. (with decomposition) from the fractions eluted with mixtures of methylene chloride and methanol ranging from 3:10 to 2:1 by volume and with methanol.

Workup

  1. additionwas introduced into the solution
  2. temperatureThe reaction mixture was then warmed
  3. customkept at 50° C. in a reaction flask
  4. customfitted with a reflux condenser
  5. temperatureAt the end of this time, the reaction mixture was cooled
  6. temperatureThe mixture was then heated
  7. temperatureunder reflux on an oil bath for 1 hour
  8. temperatureThe mixture was then cooled
  9. concentrationconcentrated by evaporation under reduced pressure
  10. additionMethanol was added to the residue
  11. filtrationan insoluble material was filtered off

Sources & evidence

ORD record
ord-989cd33d44c14367836e47f2a279fa92
Source dataset
uspto-grants-1991_11
Patent number
US05068340

Reaction notes

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