반응 #512063

반응 방정식

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

N-methyl imidazole

3-Benzoylpropionic acid

p-toluenesulfonyl chloride

→

desired product

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

용매

CH2Cl2

CH2Cl2

반응 조건

후처리

1. 1
   workup.ADDITIONis added dropwise
2. 2
   농축concentrated in vacuo
3. 3
   workup.DISSOLUTIONThe resulting residue is dissolved in EtOAc
4. 4
   세척washed with 1N HCl and brine
5. 5
   건조The solution is dried over Na2SO4
6. 6
   여과filtered
7. 7
   농축concentrated
8. 8
   기타the crude material purified over silica

실험 절차

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 p-toluenesulfonyl 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.

출처