tert-Butylsulfinamide, (S)-(-)- → (S)-ethyl 2-(tert-butylsulfinylimino)-4-fluoro-3,3-dimethylbutanoate

HRID 520359

반응식

HRID 520359 반응식
[F:1][CH2:2][C:3]([CH3:12])([CH3:11])[C:4](=O)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH3:13][C:14]([S@@:17]([NH2:19])=[O:18])([CH3:16])[CH3:15]>C1COCC1.CCOC(C)=O.[Na+].[Cl-].C(O[Ti](OCC)(OCC)OCC)C>[C:14]([S@@:17]([N:19]=[C:4]([C:3]([CH3:12])([CH3:11])[CH2:2][F:1])[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[O:18])([CH3:16])([CH3:15])[CH3:13]

참가 물질

7

반응물 2

HCID 11355477tert-Butylsulfinamide, (S)-(-)-HCID 86690078Ethyl 4-fluoro-3,3-dimethyl-2-oxobutanoate

생성물 1

HCID 86690079(S)-ethyl 2-(tert-butylsulfinylimino)-4-fluoro-3,3-dimethylbutanoate수율 30.2%

시약·촉매·용매 4

HCID 178477244HCID 178477244, 화합물촉매HCID 5234Sodium Chloride용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

반응 조건

온도
65 °C

실험 절차

To a solution of ethyl 4-fluoro-3,3-dimethyl-2-oxobutanoate (2.3 g, 13.05 mmol) in THF (20 mL) was added (S)-2-methylpropane-2-sulfinamide (1.899 g, 15.67 mmol) and tetraethoxytitanium (5.91 mL, 26.1 mmol). The reaction mixture was heated at 65° C. for 6 h. The reaction mixture was cooled down, diluted with EtOAc and sat. NaCl (40 mL) and stirred at rt for 0.5 h. The solid was filtered and washed with water and EtOAc. The filtrate was separated and the organic layer was washed with water, sat. NaCl, dried (MgSO4) and purified by flash chromatography (EtOAc/hexane) to afford (S)-ethyl 2-(tert-butylsulfinylimino)-4-fluoro-3,3-dimethylbutanoate (1.1 g). 1H NMR (400 MHz, CDCl3) δ ppm 4.46-4.53 (1H, m), 4.28-4.42 (3H, m), 1.59 (3H, s), 1.21-1.31 (15H, m).

후처리

  1. temperatureThe reaction mixture was cooled down
  2. filtrationThe solid was filtered
  3. washwashed with water and EtOAc
  4. customThe filtrate was separated
  5. washthe organic layer was washed with water, sat. NaCl
  6. dry with materialdried (MgSO4)
  7. custompurified by flash chromatography (EtOAc/hexane)

출처 및 근거

ORD 기록
ord-123710cb3b9642a2a1939182945b1418
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09326973B2

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