Trifluoroacetic anhydride → Triphenylsulfonium 2-(adamantane-1-carbonyloxy)ethanesulfonate

HRID 1943564

반응식

HRID 1943564 반응식
[S:1]([CH2:5][CH2:6][OH:7])([O-:4])(=[O:3])=[O:2].[Na+].[C:9]12([C:19](O)=[O:20])[CH2:18][CH:13]3[CH2:14][CH:15]([CH2:17][CH:11]([CH2:12]3)[CH2:10]1)[CH2:16]2.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[Cl-].[C:36]1([S+:42]([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.C(=O)(O)[O-].[Na+]>FC(F)(F)C(O)=O.C(Cl)Cl.O>[C:9]12([C:19]([O:7][CH2:6][CH2:5][S:1]([O-:4])(=[O:3])=[O:2])=[O:20])[CH2:16][CH:15]3[CH2:14][CH:13]([CH2:12][CH:11]([CH2:17]3)[CH2:10]1)[CH2:18]2.[C:49]1([S+:42]([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=1

참가 물질

9

반응물 5

HCID 9845Trifluoroacetic anhydrideHCID 132351-Adamantanecarboxylic acidHCID 61343Triphenylsulfonium chlorideHCID 516892Sodium BicarbonateHCID 517063Sodium Isethionate

생성물 1

HCID 86642232Triphenylsulfonium 2-(adamantane-1-carbonyloxy)ethanesulfonate수율 62%

시약·촉매·용매 3

HCID 962Water용매HCID 6344Dichloromethane용매HCID 6422Trifluoroacetic acid용매

실험 절차

In 125 g of trifluoroacetic acid were dissolved 14.8 g (0.10 mole) of sodium isethionate and 18.0 g (0.10 mole) of 1-adamantanecarboxylic acid. To this solution, 32.0 g (0.15 mole) of trifluoroacetic anhydride was added dropwise, followed by stirring for 2 hours at room temperature. Then 430 g (0.15 mole) of an aqueous solution of triphenylsulfonium chloride prepared in Synthesis Example 1-1, 800 g of water, and 1,500 g of methylene chloride were added, followed by stirring for 1 hour at room temperature. At the end of stirring, the organic layer was taken out, aqueous sodium bicarbonate was added dropwise until the pH of the aqueous layer ceased to be acidic, and the organic layer was then taken out. The organic layer was washed with water and concentrated in vacuum. Methyl isobutyl ketone was added to the concentrate, which was concentrated in vacuum again while distilling off the residual water. Diisopropyl ether was added to the residue for recrystallization. The crystals were collected and dried, obtaining the target compound, triphenylsulfonium 2-(adamantane-1-carbonyloxy)ethanesulfonate. White crystals, 34.1 g, yield 62%. The compound, designated PAG-1, has the following structure.

후처리

  1. additionwere added
  2. stirringby stirring for 1 hour at room temperature
  3. stirringAt the end of stirring
  4. washThe organic layer was washed with water
  5. concentrationconcentrated in vacuum
  6. additionMethyl isobutyl ketone was added to the concentrate, which
  7. concentrationwas concentrated in vacuum again
  8. distillationwhile distilling off the residual water
  9. additionDiisopropyl ether was added to the residue for recrystallization
  10. customThe crystals were collected
  11. customdried

출처 및 근거

ORD 기록
ord-e594ef7332c24e08b2be557c4bd48e27
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08394570B2

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