Ethyl Acetate → 2-(2-Ethanesulfonyl-1-hydroxy-1-methyl-ethyl)-6-trifluoromethyl-1H-indole-5-carbonitrile

HRID 32945노트

반응식

HRID 32945 반응식
C(S[CH2:4][C:5]([C:8]1[NH:9][C:10]2[C:15]([CH:16]=1)=[CH:14][C:13]([C:17]#[N:18])=[C:12]([C:19]([F:22])([F:21])[F:20])[CH:11]=2)([OH:7])[CH3:6])C.C(=O)(O)[O-].[Na+].[OH:28][O:29][S:30]([O-:32])=[O:31].[K+:33].[C:34](OCC)(=O)[CH3:35]>[N+](CCCC)(CCCC)(CCCC)CCCC.[O-]S(O)(=O)=O>[OH:28][O:29][S:30]([O-:32])=[O:31].[K+:33].[CH2:34]([S:30]([CH2:6][C:5]([C:8]1[NH:9][C:10]2[C:15]([CH:16]=1)=[CH:14][C:13]([C:17]#[N:18])=[C:12]([C:19]([F:22])([F:20])[F:21])[CH:11]=2)([OH:7])[CH3:4])(=[O:32])=[O:29])[CH3:35]

참가 물질

7

반응물 4

HCID 8857Ethyl Acetate3회HCID 516892Sodium BicarbonateHCID 117096572-(2-Ethylsulfanyl-1-hydroxy-1-methyl-ethyl)-6-trifluoromethyl-1H-indole-5-carbonitrileHCID 23707502Potassium hydroxy sulfite

생성물 2

HCID 115522382-(2-Ethanesulfonyl-1-hydroxy-1-methyl-ethyl)-6-trifluoromethyl-1H-indole-5-carbonitrileHCID 23707502Potassium hydroxy sulfite

시약·촉매·용매 1

HCID 94433Tetrabutylammonium hydrogen sulfate촉매

실험 절차

The (−) enantiomer of 2-(2-ethylsulfanyl-1-hydroxy-1-methyl-ethyl)-6-trifluoromethyl-1H-indole-5-carbonitrile, the compound prepared as in Example 86 above (1 equivalent) was dissolved in ethyl acetate (5 mL/mmol). A separate aqueous solution of OXONE® (3 equivalents) and Bu4NHSO4 (0.3 mol %) (10 mL water/g of OXONE®) was prepared and the pH of this solution adjusted to about 7 by the addition of saturated sodium bicarbonate solution. After the pH adjustment, this aqueous solution was added to the ethyl acetate solution and the resulting biphasic mixture vigourously stirred. After 8 hours, an additional 3 equivalents of the pH-adjusted OXONE® solution was added and the mixture stirred overnight. Ethyl acetate (10 mummol of sulfide) was added and the aqueous phase was removed. The organic phase was washed with brine, dried over anhydrous Na2SO4, concentrated to yield a yellow solid. This crude material (yellow solid) was purified using column chromatography (silica gel, ethyl acetate as eluent) to yield the title compound as a pale yellow solid.

후처리

  1. stirringthe mixture stirred overnight
  2. customthe aqueous phase was removed
  3. washThe organic phase was washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. customto yield a yellow solid
  7. customThis crude material (yellow solid) was purified

출처 및 근거

ORD 기록
ord-3f3b2dc8c94240e484409ac6ac788f78
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07427682B2

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