Reaction #158274

Reaction equation

HATU

5-chloro-2-(4-chlorophenyl)-2-methylpentanoic acid

3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)benzohydrazide

triethylamine

→

title compound

Yield 82.6%

N′-[5-chloro-2-(4-chlorophenyl)-2-methylpentanoyl]-3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)benzohydrazide

Yield 82.6%

Solvents

ethyl acetate

water

brine

DMF

Conditions

Workup

1. 1
   Extractionthe mixture was extracted with ethyl acetate
2. 2
   WashThe extract was washed with saturated brine (4×50 mL)
3. 3
   Dryingdried over anhydrous magnesium sulfate
4. 4
   Otherthe solvent was evaporated under reduced pressure
5. 5
   OtherThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Procedure

To a mixture of 5-chloro-2-(4-chlorophenyl)-2-methylpentanoic acid (6.34 g), 3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)benzohydrazide (5.0 g) and triethylamine (6.78 mL) in DMF (50 mL) was added HATU (9.23 g) at 0° C., and the mixture was stirred at room temperature for 14 hr. The reaction mixture was diluted with ethyl acetate (50 mL), water (150 mL) and saturated brine (50 mL), and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine (4×50 mL), and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (8.19 g).

Source