Reaction #88319

Reaction equation

(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

Solvents

CH2Cl2

CH2Cl2

Conditions

Workup

1. 1
   workup.ADDITIONis added dropwise
2. 2
   Concentrationconcentrated in vacuo
3. 3
   workup.DISSOLUTIONThe resulting residue is dissolved in EtOAc
4. 4
   Washwashed with 1N HCl and brine
5. 5
   DryingThe solution is dried over Na2SO4
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated
8. 8
   Otherthe crude material purified over silica

Procedure

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.

Source