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Pregled bibliografske jedinice broj: 391414

Process for Production of (S)-N-Pentanoyl-N-[[2'-(1H-tetrazole-5-yl[1, 1'-biphenyl]-4-yl]methyl]-L-valine


Cepanec, Ivica; Litvić, Mladen; Koretić, Štefanija; Bartolinčić, Anamarija; Drušković, Vinka; Šporec, Anita
Process for Production of (S)-N-Pentanoyl-N-[[2'-(1H-tetrazole-5-yl[1, 1'-biphenyl]-4-yl]methyl]-L-valine
(2005)


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Naslov
Process for Production of (S)-N-Pentanoyl-N-[[2'-(1H-tetrazole-5-yl[1, 1'-biphenyl]-4-yl]methyl]-L-valine

Autori
Cepanec, Ivica ; Litvić, Mladen ; Koretić, Štefanija ; Bartolinčić, Anamarija ; Drušković, Vinka ; Šporec, Anita

Broj patenta
WO2005049586

Godina
2005

Datum patenta
02.06.2005.

Nositelj prava
BELUPO d.d., Zagreb, Hrvatska

Sažetak
The patent relates to a new process of synthesis of an antihypertensive agent, N-pentanoyl-N-[[2'-(1H-tetrazole-5-yl)[1, 1'-biphenyl]-4-yl]methyl]-L-valine (1), also known under the generic name of valsartan, by selective reaction of N-pentanoyl-N-[[2'-(1H-tetrazole-5-yl) [1, 1'-biphenyl]-4-yl]methyl]-L-valine methyl-ester (14) with metallic or quaternary ammonium trialkylsilanolates by SN2 reaction. The compound 14 was produced in four reaction steps starting from 2N-trityl-5-(4'-methylbiphenyl-2-yl)tetrazole (17) and L-valine methyl-ester (11). Free-radical bromination of the compound 17 with N-bromosuccinimide produced 2N-trityl-5-(4'-bromomethylbiphenyl-2-yl)tetrazole (7), which in the reaction with L-valine methyl-ester (11) results in N-[[2'-(2N-trityl-tetrazole-5-yl)[1, 1'-biphenyl]-4yl]methyl]-L-valine methyl-ester hydrobromide (15). ; Acylation of the compound 15 with pentanoyl chloride in the presence of trialkylamine bases results in N-pentanoyl-N-[[2'-(2Ntrityl-tetrazole-5-yl)[1, 1'-biphenyl] -4-yl]methyl]-L-valine methyl-ester (16). Removal of trityl protecting group by strong acids produces the key intermediary, compound 14.

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Farmacija

Citiraj ovu publikaciju

Cepanec, Ivica; Litvić, Mladen; Koretić, Štefanija; Bartolinčić, Anamarija; Drušković, Vinka; Šporec, Anita
Process for Production of (S)-N-Pentanoyl-N-[[2'-(1H-tetrazole-5-yl[1, 1'-biphenyl]-4-yl]methyl]-L-valine
(2005)
BELUPO d.d. (2005) Process for Production of (S)-N-Pentanoyl-N-[[2'-(1H-tetrazole-5-yl[1, 1'-biphenyl]-4-yl]methyl]-L-valine, WO2005049586.
@patent{patent, year = {2005}, keywords = {}, title = {Process for Production of (S)-N-Pentanoyl-N-[[2'-(1H-tetrazole-5-yl[1, 1'-biphenyl]-4-yl]methyl]-L-valine}, keyword = {}, publisherplace = {Zagreb} }
@patent{patent, year = {2005}, keywords = {}, title = {Process for Production of (S)-N-Pentanoyl-N-[[2'-(1H-tetrazole-5-yl[1, 1'-biphenyl]-4-yl]methyl]-L-valine}, keyword = {}, publisherplace = {Zagreb} }




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