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

HRID 5621

반응식

HRID 5621 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8078Cyclohexane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7aa6ea05ad5f4e639b91d1a44ecf298b
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05245056

연결된 노트

불러오는 중…