Reaction #439558

Reaction equation

(R)-(−)-2-oxo-3-tert-butoxycarbonylamino-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

1-chloropinacolone

potassium carbonate

→

title compound

Yield 99.8%

(R)-1-tert-butylcarbonylmethyl-2-oxo-3-tert-butoxycarbonylamino-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

Yield 99.8%

Solvents

dimethylsulfoxide

Conditions

Workup

1. 1
   OtherThe precipitate thus formed
2. 2
   Filtrationwas collected by filtration with suction
3. 3
   Washwashed with water
4. 4
   Otherdried

Procedure

To a solution of 50 g of (R)-(−)-2-oxo-3-tert-butoxycarbonylamino-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine in 200 ml of dimethylsulfoxide were added 28.1 g of 1-chloropinacolone, 28.8 g of potassium carbonate (powder), 1.15 g of potassium iodide and 1.35 g of tetrabutylammonium bromide. The mixture was stirred at room temperature for 4 hours. The reaction mixture was poured into ice water. The precipitate thus formed was collected by filtration with suction, washed with water and then dried, whereby 63.5 g of the title compound was obtained.

Source