4-Hydroxy Valsartan, Mixture of Diastereomers Chemical Properties

Melting point:

130-132°C

storage temp. 

Hygroscopic, -20°C Freezer, Under Inert Atmosphere

solubility 

Methanol (Slightly)

form 

Solid

color 

White to Off-White

Stability:

Hygroscopic

CAS DataBase Reference

188259-69-0

4-Hydroxy Valsartan, Mixture of Diastereomers Usage And Synthesis

Description

4-hydroxy Valsartan is a major metabolite of the angiotensin II type 1 (AT₁) receptor antagonist valsartan . It reduces platelet aggregation induced by epinephrine and collagen but not ADP in human whole blood.

Chemical Properties

White Solid

Uses

A nonpeptide angiotensin II AT1-receptor antagonist.

Definition

ChEBI: 4-Hydroxyvalsartan is a valine derivative.

Synthesis

8.64 g of benzyl (S)-2-[(2-cyanobiphenyl-4-ylmethyl)-(4-oxo-pentanoyl)-amino]-3-methyl-butanoate in 20 ml of xylene and 12.71 g of Tributyltinazid (Aldrich) were refluxed for 28 hours. The mixture was treated with 0.5N aqueous sodium hydroxide, the aqueous phase was washed with ether and the ether phase was extracted once with water. The combined aqueous phases were acidified with concentrated aqueous hydrochloric acid, extracted with dichloromethane, washed with water, suspended in activated carbon, filtered, dried with sodium sulfate, concentrated and dried under vacuum. The product (S)-3-methyl-2-{(4-oxo-pentanoyl)-[2-(1H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-amino}-butanoic acid benzyl ester was obtained as a brown foam. 7.9 g of benzyl (S)-3-methyl-2-{(4-oxo-pentanoyl)-[2-(1H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-amino}-butanoate in 160 ml of tetrahydrofuran was hydrogenated in the presence of 1.5 g of lapped palladium-carbon (10%) at atmospheric pressure and room temperature until saturation was reached. The mixture was filtered and concentrated in vacuo to afford (S)-3-methyl-2-{(4-oxo-pentanoyl)-[2-(1H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-amino}-butanoic acid as almost white foam

References

[1] VICTOR L SEREBRUANY. Effects of valsartan and valeryl 4-hydroxy valsartan on human platelets: a possible additional mechanism for clinical benefits.[J]. Journal of Cardiovascular Pharmacology, 2004, 43 5: 677-684. DOI: 10.1097/00005344-200405000-00010

4-Hydroxy Valsartan, Mixture of Diastereomers(188259-69-0)Related Product Information

• Valsartan
• Isoleucine Valsartan
• Valsartan Desvaleryl Impurity
• Valsartan n-Propyl
• Valsartan Impurity 1
• L-VALINE, N-[(2'-CYANO[1,1'-BIPHENYL]-4-YL)METHYL]-, METHYL ESTER, MONOHYDROCHLORIDE
• Valsartan Impurity 10
• Valsartan Impurity 5
• Valsartan Methyl Ester
• Pentanamide, N-(diazirino[1,3-f]phenanthridin-4-ylmethyl)-N-(2-methylpropyl)-
• Valsartan Impurity 12
• Valsartan Impurity 3
• ethyl N-((2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)Methyl)-N-pentanoyl-L-valinate
• 5-[2-(4'-METHYLBIPHENYL)]TETRAZOLE
• Valsartan Related Compound A
• Valsartan cyano analog methyl ester
• Valsartan Impurity 26
• L-Valine, N-[(2'-cyano[1,1'-biphenyl]-4-yl)methyl]-N-(1-oxopropyl)-, methyl ester