تفاعل #40874

معادلة التفاعل

N-(4-iodobenzyl)-N-valeryl-L-valine

2-(1H-tetrazol-5-yl)phenylboronic acid

NaOH

→

Valsartan

المردود 85.1%

المذيبات

methanol

water

ظروف التفاعل

المعالجة

1. 1
   أخرىNitrogen is bubbled for 5 min
2. 2
   workup.ADDITIONare added
3. 3
   أخرىOnce 3 h
4. 4
   workup.DISTILLATIONthe methanol is distilled
5. 5
   workup.ADDITIONThe crude product is treated with 25 mL of HCl 1N and 25 mL of AcOEt
6. 6
   تجفيفThe AcOEt phase is dried with anhydrous sodium sulphate
7. 7
   workup.DISTILLATIONafter distilling the solvent the crude product
8. 8
   أخرىobtained
9. 9
   أخرىis purified by silica gel chromatography (eluent AcOEt/heptane/AcOH 1.5:5:0.2)

الإجراء التجريبي

Nitrogen is bubbled for 5 min. To a mixture made up of 0.20 g (0.48 mmol) of N-(4-iodobenzyl)-N-valeryl-L-valine, 0.115 g (0.61 mmol) of 2-(1H-tetrazol-5-yl)phenylboronic acid, 0.017 g (0.024 mmol) of bis(triphenylphosphine)palladium chloride and 0.115 g (2.87 mmol) of NaOH in 2.4 mL of methanol and 0.7 mL of water are added. The reaction is heated to 70° C. under nitrogen atmosphere. Once 3 h has elapsed the reaction is considered to be completed and the methanol is distilled. The crude product is treated with 25 mL of HCl 1N and 25 mL of AcOEt. The AcOEt phase is dried with anhydrous sodium sulphate and after distilling the solvent the crude product obtained is purified by silica gel chromatography (eluent AcOEt/heptane/AcOH 1.5:5:0.2) to provide 0.178 g (85%) of Valsartan.

المصدر