تفاعل #1076913

معادلة التفاعل

cyanoacetamide

HCl

3-amino-6-phenyl-hexan-2-ol

sodium

potassium carbonate

trifluoromethanesulphonic anhydride

triflyl azide

sodium azide

→

foam

المردود 12.0%

5-Amino-1-[1-(1-hydroxy-ethyl)-4-phenyl-butyl]-1H-[1,2,3]triazole-4-carboxamide

المردود 12.0%

المذيبات

methanol

ethanol

ethanol

dichloromethane

dichloromethane

water

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   أخرىThe phases are separated
2. 2
   استخلاصthe aqueous phase is extracted twice with dichloromethane
3. 3
   غسيلthe combined organic phases are washed with saturated sodium bicarbonate solution
4. 4
   workup.STIRRINGThe mixture is stirred at room temperature for 15 hours
5. 5
   استخلاصextracted with dilute ammonia solution and with EDTA solution
6. 6
   تجفيفdried over sodium sulphate
7. 7
   تركيزconcentrated
8. 8
   أخرىa rotary evaporator
9. 9
   workup.DISSOLUTIONThis gives 331 mg of an oil which is dissolved in 1 ml of DMSO
10. 10
    workup.STIRRINGthe mixture is stirred at room temperature for 15 hours
11. 11
    استخلاصextracted three times with dichloromethane
12. 12
    أخرىChromatographic purification

الإجراء التجريبي

At 0° C., 1.19 g(18.3 mmol) of sodium azide in a mixture of 3 ml of water and 5 ml of dichloromethane are mixed dropwise with 1.046 g (mmol) of trifluoromethanesulphonic anhydride, and the resulting mixture is stirred at 0° C. for 2 hours. The phases are separated, the aqueous phase is extracted twice with dichloromethane and the combined organic phases are washed with saturated sodium bicarbonate solution. 386 mg (2 mmol) of 3-amino-6-phenyl-hexan-2-ol are dissolved in 2 ml of methanol and admixed successively with 10 mg of copper sulphate and 10 mg of potassium carbonate. The solution of the triflyl azide in dichloromethane is added and the mixture is made up to a total volume of 20 ml using dichloromethane. The mixture is stirred at room temperature for 15 hours, extracted with dilute ammonia solution and with EDTA solution, dried over sodium sulphate and concentrated using a rotary evaporator. This gives 331 mg of an oil which is dissolved in 1 ml of DMSO and admixed with a solution of 75 mg (3.5 mmol) of sodium in 1 ml of ethanol. 197 mg (2.34 mmol) of cyanoacetamide and, after 30 minutes, 2 ml of ethanol are added, and the mixture is stirred at room temperature for 15 hours. The mixture is poured into 30 ml of ice-water and, after addition of 3 ml of 1N HCl, extracted three times with dichloromethane and once with ethyl acetate. Chromatographic purification gives 72 mg (12%) of a foam.

المصدر