Hydrochloric Acid → HCID 18419355, compound

Temperature

0 °C

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.

1. customThe phases are separated
2. extractionthe aqueous phase is extracted twice with dichloromethane
3. washthe combined organic phases are washed with saturated sodium bicarbonate solution
4. stirringThe mixture is stirred at room temperature for 15 hours
5. extractionextracted with dilute ammonia solution and with EDTA solution
6. dry with materialdried over sodium sulphate
7. concentrationconcentrated
8. customa rotary evaporator
9. dissolutionThis gives 331 mg of an oil which is dissolved in 1 ml of DMSO
10. stirringthe mixture is stirred at room temperature for 15 hours
11. extractionextracted three times with dichloromethane
12. customChromatographic purification

ORD record

ord-653501b1d466433e88c5dd781d3be7a9

Source dataset

uspto-grants-2002_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06458796B1