反応 #650442

反応方程式

D-allo-threonine

K2CO3

4-fluoro-2-(trifluoromethyl)benzonitrile

→

title compound

収率 100.0%

(2R,3R)-2-(4-Cyano-3-(trifluoromethyl)phenylamino)-3-hydroxybutanoic acid

収率 100.0%

溶媒

DMSO

反応条件

後処理

1. 1
   温度to cool to room temperature
2. 2
   その他quenched with H2O (400 mL)
3. 3
   抽出extracted with EtOAc (3×200 mL)
4. 4
   抽出extracted with EtOAc (2×100 mL)
5. 5
   洗浄washed with H2O (3×100 mL)
6. 6
   乾燥dried (Na2SO4)
7. 7
   ろ過filtered
8. 8
   濃縮concentrated under reduced pressure

実験手順

To a suspension of D-allo-threonine (4.30 g, 36.1 mmol) and K2CO3 (8.73 g, 63.2 mmol) in DMSO (50 mL) was added 4-fluoro-2-(trifluoromethyl)benzonitrile (5.69 g, 30.1 mmol) at room temperature. The reaction mixture was heated to 75° C. and stirred for 39 h. The reaction mixture was allowed to cool to room temperature and quenched with H2O (400 mL) and extracted with EtOAc (3×200 mL). The aqueous layer was then acidified with solid citric acid and extracted with EtOAc (2×100 mL). The later organic extracts were combined, washed with H2O (3×100 mL), dried (Na2SO4), filtered and concentrated under reduced pressure to provided the title compound as a brown oil (8.67 g, 100%): 1H NMR (400 MHz, acetone-d6, δ in ppm) 7.69 (d, J=8.6 Hz, 1H), 7.30 (d, J=2.5 Hz, 1H), 7.07 (dd, J=2.5, 8.4 Hz, 1H), 6.54 (d, J=8.4 Hz, 1H), 4.35 (dd, J=4.9, 8.4 Hz, 1H), 4.29 (dq, J=4.9, 6.5 Hz, 1H), 1.32 (d, J=6.4 Hz, 3H).

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