Réaction #161034

Équation de réaction

N,N-diisopropylethylamine

N-[[1-[[(phenylmethoxy)carbonyl]amino]cyclohexyl]carbonyl]-L-valinol

→

title compound

Rendement 77.0%

N-[[1-[[(Phenylmethoxy)carbonyl]amino]cyclohexyl]carbonyl]-L-valinal

Rendement 77.0%

Solvants

dimethyl sulfoxide

methylene chloride

dimethyl sulfoxide

Conditions de réaction

Traitement

1. 1
   Températurecooling
2. 2
   TempératureFurther, under ice-cooling
3. 3
   workup.STIRRINGthe mixture was stirred at the same temperature for 2 hours
4. 4
   Extractionextracted with ethyl acetate twice
5. 5
   LavageAfter the organic layer was washed with a 10% aqueous citric acid solution
6. 6
   Séchagea saturated aqueous sodium hydrogencarbonate solution and then saturated brine and dried with anhydrous magnesium sulfate
7. 7
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
8. 8
   workup.ADDITION20 ml of diisopropyl ether was added to the residue
9. 9
   workup.STIRRINGthe mixture was stirred at room temperature for 18 hours
10. 10
    FiltrationThe obtained crystal was collected by filtration

Mode opératoire

Under an argon gas atmosphere, 1.22 g (9.44 mmol) of N,N-diisopropylethylamine was added dropwise to a solution of 1.50 g (9.44 mmol) of sulfur trioxide-pyridine complex in 10 ml of anhydrous dimethyl sulfoxide and 5 ml of anhydrous methylene chloride under ice-cooling, and the mixture was stirred for 15 minutes. Further, under ice-cooling, a solution of 570 mg (1.57 mmol) of N-[[1-[[(phenylmethoxy)carbonyl]amino]cyclohexyl]carbonyl]-L-valinol in 3 ml of anhydrous dimethyl sulfoxide was added to the reaction solution, and the mixture was stirred at the same temperature for 2 hours. The reaction solution was poured to ice-water and extracted with ethyl acetate twice. After the organic layer was washed with a 10% aqueous citric acid solution, a saturated aqueous sodium hydrogencarbonate solution and then saturated brine and dried with anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. 20 ml of diisopropyl ether was added to the residue, and the mixture was stirred at room temperature for 18 hours. The obtained crystal was collected by filtration to obtain 435 mg (77%) of the title compound.

Source