tert-Butylsulfinamide, (S)-(-)- → tert-butyl 3-[2-[(E)-[(S)-tert-butylsulfinyl]iminomethyl]-3-methylphenyl]propanoate

HRID 64426

반응식

HRID 64426 반응식
[CH:1]([C:3]1[C:8]([CH3:9])=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:10][CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=O.[CH3:19][C:20]([S@@:23]([NH2:25])=[O:24])([CH3:22])[CH3:21]>C1COCC1.CCO.CCO.CCO.CCO.[Ti]>[C:20]([S@@:23](/[N:25]=[CH:1]/[C:3]1[C:8]([CH3:9])=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:10][CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[O:24])([CH3:22])([CH3:21])[CH3:19]

참가 물질

5

반응물 2

HCID 11355477tert-Butylsulfinamide, (S)-(-)-HCID 86713435Tert-butyl 3-(2-formyl-3-methylphenyl)propanoate

생성물 1

HCID 90072800tert-butyl 3-[2-[(E)-[(S)-tert-butylsulfinyl]iminomethyl]-3-methylphenyl]propanoate수율 77.8%

시약·촉매·용매 2

HCID 2724286Titanium(IV)ethoxide촉매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 305 mg of tert-butyl 3-(2-formyl-3-methylphenyl)propanoate in 3 ml of THF 3 ml were added 298 mg of (S)-2-methyl-2-propanesulfinamide and 0.62 ml of tetraethyl orthotitanate, followed by stirring at room temperature for 16 hours. The reaction mixture was poured into ice water and the insoluble material was filtered through Celite. To the filtrate was added chloroform to carry out a layer separation operation. The organic layer was washed with water and subsequentially with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 336 mg of tert-butyl 3-{2-[(E)-{[(S)-tert-butylsulfinyl]imino}methyl]-3-methylphenyl}propanoate.

후처리

  1. filtrationthe insoluble material was filtered through Celite
  2. additionTo the filtrate was added chloroform
  3. customa layer separation operation
  4. washThe organic layer was washed with water and subsequentially with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-2acaaa5049f34efc927e8517584e58cd
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447090B2

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