反応 #88319

反応方程式

(S)-1-(4-ethylthiazol-2-yl)-2-(4-nitrophenyl)ethanamine

N-methyl imidazole

3-Benzoylpropionic acid

thionyl chloride

→

desired product

(S)—N-[1-(4-ethylthiazol-2-yl)-2-(4-nitrophenyl)ethyl]-4-oxo-4-phenylbutanamide

溶媒

CH2Cl2

CH2Cl2

反応条件

後処理

1. 1
   workup.ADDITIONis added dropwise
2. 2
   濃縮concentrated in vacuo
3. 3
   workup.DISSOLUTIONThe resulting residue is dissolved in EtOAc
4. 4
   洗浄washed with 1N HCl and brine
5. 5
   乾燥The solution is dried over Na2SO4
6. 6
   ろ過filtered
7. 7
   濃縮concentrated
8. 8
   その他the crude material purified over silica

実験手順

3-Benzoylpropionic acid (0.250 g) is dissolved in CH2Cl2 (5 mL), N-methyl imidazole (0.333 mL) is added and the resulting solution is cooled to 0° C. after which a solution of thionyl chloride (0.320 g) in CH2Cl2 (2 mL) is added dropwise. After 0.5 hours (S)-1-(4-ethylthiazol-2-yl)-2-(4-nitrophenyl)ethanamine, 3, (0.388 g) is added. The reaction is stirred for 18 hours at room temperature and then concentrated in vacuo. The resulting residue is dissolved in EtOAc and washed with 1N HCl and brine. The solution is dried over Na2SO4, filtered, and concentrated and the crude material purified over silica to afford 0.415 g of the desired product.

出典