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

HRID 520359

反応式

HRID 520359 の反応式
[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]

参加物

7

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 178477244HCID 178477244、化合物触媒HCID 5234Sodium Chloride溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
65 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-123710cb3b9642a2a1939182945b1418
出典データセット
uspto-grants-2016_05
特許番号
US09326973B2

関連ノート

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