Trifluoromethanesulfonic acid → Methyl (3R)-3-(benzyloxy)tetradecanoate

HRID 1609353Notes

Reaction equation

HRID 1609353 reaction equation
[OH:1][C@H:2]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:3][C:4]([O:6][CH3:7])=[O:5].ClC(Cl)(Cl)C(=N)O[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.FC(F)(F)S(O)(=O)=O>C1CCCCC1>[CH2:23]([O:1][C@H:2]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:3][C:4]([O:6][CH3:7])=[O:5])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 62406Trifluoromethanesulfonic acidHCID 144968Benzyl 2,2,2-trichloroacetimidateHCID 98349453R-hydroxymyristic acid methyl ester

Product 1

HCID 13817922Methyl (3R)-3-(benzyloxy)tetradecanoateYield 112.8%

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

A suspension of 206.7 g of methyl (R)-3-hydroxytetradecanoate in 1000 ml of cyclohexane was treated under nitrogen and while stirring with 214.2 g of benzyl trichloroacetimidate and dissolved at 20°. 10 ml of trifluoromethanesulphonic acid were added dropwise while cooling in an ice/water bath in such a manner that the temperature remains between 20°-23°. The resulting suspension was stirred at 25°-30°. The precipitate was filtered off, the filter cake was washed with cyclohexane, the filtrates were extracted with sat. NaHCO3 solution, water and sat. NaCl solution. The organic phase was dried over magnesium sulphate, filtered, the filter cake was washed with cyclohexane and the filtrates were evaporated. 314.5 g of methyl (R)-3-(benzyloxy)-tetradecanoate were obtained.

Workup

  1. additionwas treated under nitrogen
  2. dissolutiondissolved at 20°
  3. temperaturewhile cooling in an ice/water bath in such a manner that the temperature
  4. customremains between 20°-23°
  5. filtrationThe precipitate was filtered off
  6. washthe filter cake was washed with cyclohexane
  7. extractionthe filtrates were extracted with sat. NaHCO3 solution, water and sat. NaCl solution
  8. dry with materialThe organic phase was dried over magnesium sulphate
  9. filtrationfiltered
  10. washthe filter cake was washed with cyclohexane
  11. customthe filtrates were evaporated

Sources & evidence

ORD record
ord-2340f364541d486da0ed72f2602acaad
Source dataset
uspto-grants-1995_03
Patent number
US05399720

Reaction notes

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