Reaction #4225

Reaction equation

2-amino-2,3-dimethyl-butyric acid amide

triethylamine

monoethyl 2,3-dimethylfumarate chloride

→

monoethyl-2,3-dimethylfumarate N-(1-aminocarbonyl-1-methylisobutyl)-amide

Yield 42.3%

Solvents

methylene chloride

methylene chloride

Conditions

Workup

1. 1
   workup.STIRRINGThe mixture was stirred for 2 hours at room temperature
2. 2
   Extractionthe resulting solution was extracted with water, with 2N hydrochloric acid and again with water
3. 3
   Otherdried
4. 4
   Otherevaporated
5. 5
   OtherThe residue was triturated with diethyl ether
6. 6
   Filtrationsuction-filtered
7. 7
   Otherrecrystallized from a little ethanol

Procedure

A solution of 13 g of monoethyl 2,3-dimethylfumarate chloride in 20 ml of methylene chloride was added dropwise, while stirring and cooling with ice, to a solution of 12 g of 2-amino-2,3-dimethyl-butyric acid amide and 12 ml of triethylamine in 80 ml of methylene chloride. The mixture was stirred for 2 hours at room temperature, the resulting solution was extracted with water, with 2N hydrochloric acid and again with water, then dried and evaporated. The residue was triturated with diethyl ether, suction-filtered and recrystallized from a little ethanol. 8.0 g (41% of theory) of monoethyl-2,3-dimethylfumarate-N-(1-aminocarbonyl-1-methylisobutyl)-amide were obtained, m.p. 122°-125° C.

Source