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tert-Butylsulfinamide, (S)-(-)- → (NE,S)-2-methyl-N-[2,2,2-trifluoro-1-[4-(6,6,6-trifluorohexoxy)phenyl]ethylidene]propane-2-sulfinamide

HRID 1629767
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HRID 1629767 반응식
[F:1][C:2]([F:22])([F:21])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([F:20])([F:19])[F:18])=[CH:7][CH:6]=1)=O.[CH3:23][C:24]([S@@:27]([NH2:29])=[O:28])([CH3:26])[CH3:25]>C1COCC1.CCCCCC.CCOC(C)=O.C(O[Ti](OCC)(OCC)OCC)C>[CH3:23][C:24]([S@@:27](/[N:29]=[C:3](\[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([F:20])([F:19])[F:18])=[CH:7][CH:6]=1)/[C:2]([F:22])([F:21])[F:1])=[O:28])([CH3:26])[CH3:25]
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참가 물질

7

반응물 2

HCID 11355477tert-Butylsulfinamide, (S)-(-)-HCID 86685857HCID 86685857, 화합물

생성물 1

HCID 89599581(NE,S)-2-methyl-N-[2,2,2-trifluoro-1-[4-(6,6,6-trifluorohexoxy)phenyl]ethylidene]propane-2-sulfinamide수율 66%

시약·촉매·용매 4

HCID 178477244HCID 178477244, 화합물촉매HCID 8028Tetrahydrofuran용매2회
HCID 8058Hexane용매
HCID 8857Ethyl Acetate용매2회

실험 절차

To a solution of Intermediate 8B (717 mg, 2.184 mmol) and (S)-2-methylpropane-2-sulfinamide (529 mg, 4.37 mmol) in THF (10 mL) was added tetraethoxytitanium (1993 mg, 8.74 mmol) in THF (20 mL). The resulting mixture was reflux for 5 h. TLC (20% EtOAc in hexane) indicated the starting ketone was completely consumed. The solvent was evaporated to afford a yellow oil. This yellow oil was dissolved in EtOAc and then washed with saturated NaHCO3 (25 mL) and a large amount of white precipitation formed which was removed by filtering through a bed of Celite®. The white precipitation was rinsed with EtOAc. The combined EtOAc solution was washed again with saturated NaHCO3, dried (MgSO4) and concentrated. The crude product was purified by silica gel chromatography (40 g silica gel, eluted with EtOAc in hexanes) to afford Intermediate 8C (620 mg, 66%).

후처리

  1. temperatureThe resulting mixture was reflux for 5 h
  2. customwas completely consumed
  3. customThe solvent was evaporated
  4. customto afford a yellow oil
  5. washwashed with saturated NaHCO3 (25 mL)
  6. customa large amount of white precipitation
  7. customformed which
  8. customwas removed
  9. filtrationby filtering through a bed of Celite®
  10. customThe white precipitation
  11. washwas rinsed with EtOAc
  12. washThe combined EtOAc solution was washed again with saturated NaHCO3
  13. dry with materialdried (MgSO4)
  14. concentrationconcentrated
  15. customThe crude product was purified by silica gel chromatography (40 g silica gel, eluted with EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-8c3c0caf30f04112a83ad239e4f9cce8
출처 데이터셋
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08791091B2

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