تفاعل #161031

معادلة التفاعل

N—[N-[(phenylmethoxy)carbonyl]-L-leucyl]-L-valinol

water

sodium carbonate

2-furancarbonyl chloride

→

title compound

المردود 86.3%

N—[N-(2-Furanylcarbonyl)-L-leucyl]-L-valinol

المردود 86.3%

المذيبات

ethyl acetate

ethyl acetate

methanol

ظروف التفاعل

المعالجة

1. 1
   ترشيحAfter the reaction solution was filtered
2. 2
   تركيزthe filtrate was concentrated under reduced pressure
3. 3
   درجة الحرارةUnder ice-cooling
4. 4
   أخرىwas returned to room temperature
5. 5
   workup.STIRRINGwas stirred overnight
6. 6
   أخرىThe aqueous layer of the reaction solution was separately collected
7. 7
   استخلاصextracted with ethyl acetate
8. 8
   غسيلafter it was washed with a 10% potassium hydrogensulfate
9. 9
   تجفيفsaturated brine, it was dried with anhydrous sodium sulfate
10. 10
    workup.DISTILLATIONThe solvent was distilled off under reduced pressure and ether
11. 11
    workup.ADDITIONwas added to the residue
12. 12
    غسيلto wash the crystal

الإجراء التجريبي

30 mg of 10% palladium-carbon was added to a solution of 350 mg (1 mmol) of N—[N-[(phenylmethoxy)carbonyl]-L-leucyl]-L-valinol obtained in Reference Example 184 in 10 ml of methanol, and the mixture was stirred under a hydrogen atmosphere at room temperature overnight. After the reaction solution was filtered, the filtrate was concentrated under reduced pressure. 10 ml of ethyl acetate, 10 ml of water and further 159 mg (1.5 mmol) of sodium carbonate were added to the residue. Under ice-cooling, a solution of 131 mg (1 mmol) of 2-furancarbonyl chloride in 3 ml of ethyl acetate was added to the mixture solution. The reaction solution was returned to room temperature and was stirred overnight. The aqueous layer of the reaction solution was separately collected and extracted with ethyl acetate. The organic layer was combined and after it was washed with a 10% potassium hydrogensulfate and then saturated brine, it was dried with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and ether was added to the residue to wash the crystal to obtain 268 mg (86%) of the title compound.

المصدر