Valsartan supplier | CasNO.137862-53-4

Name
Valsartan
EINECS 1592732-453-0
CAS No. 137862-53-4
Article Data68
CAS DataBase
Density 1.212 g/cm³
Solubility 84.99mg/L(25 oC)
Melting Point 116-117 °C
Formula C₂₄H₂₉N₅O₃
Boiling Point 684.9 °C at 760 mmHg
Molecular Weight 435.526
Flash Point 368 °C
Transport Information
Appearance white crystalline powder
Safety 26-37/39
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms L-Valine,N-(1-oxopentyl)-N-[[2'-(1H-tetrazol- 5-yl)[1,1'-biphenyl]-4-yl]methyl]-;Diovan;Diovan (TN);L-Valine, N-(1-oxopentyl)-N-((2-(1H-tetrazol-5-yl)(1,1-biphenyl)-4-yl)methyl)-;N-(p-(o-1H-Tetrazol-5-ylphenyl)benzyl)-N-valeryl-L-valine;Valsartan [USAN:INN];N-(1-n.Pentanoyl)-N-[[2'-(1H-tetrazol-5-yl)[1',1- biphenyl]-4-yl]methyl]-L-valine;Dihydrotachystero;Valsartan USP30;
PSA 112.07000
LogP 4.16170

Synthetic route

: (S)-N-(1-carboxy-2-methyl-prop-1-yl)-N-pentarloyl-N-[2'-(1H-tetrazol-5-yl)biphenyl-4-yl-methyl]amine barium salt

: 137862-53-4
N-pentanoyl-N-[[2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]-methyl]-(L)-valine

Conditions

Conditions	Yield
With hydrogenchloride; water pH=2 - 2.5;	99.9%
With hydrogenchloride In water; ethyl acetate pH=2 - 2.2; Product distribution / selectivity;
With hydrogenchloride; water In ethyl acetate pH=~ 2 - 2.5;
With hydrogenchloride In water; ethyl acetate pH=2.5 - 3.5; Product distribution / selectivity; Industry scale;

: 137863-17-3
methyl N-((2’-(1H-tetrazol-5-yl)-[1,1’-biphenyl]-4-yl)methyl)-N-pentanoyl-L-valinate

: 137862-53-4
N-pentanoyl-N-[[2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]-methyl]-(L)-valine

Conditions

Conditions	Yield
With sodium hydroxide In diethyl ether; water at 20℃;	99%
With water; sodium hydroxide In methanol at 25℃; for 12h;	95%
Stage #1: methyl N-((2’-(1H-tetrazol-5-yl)-[1,1’-biphenyl]-4-yl)methyl)-N-pentanoyl-L-valinate With sodium hydroxide In water at 20℃; for 20h; Stage #2: With hydrogenchloride; water pH=2;	93%

: 781664-81-1
N-[[2'-(1-triphenylmethyltetrazol-5yl)biphenyl-4-yl]methyl]-N-valeryl-L-valine methyl ester

: 137862-53-4
N-pentanoyl-N-[[2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]-methyl]-(L)-valine

Conditions

Conditions	Yield
Stage #1: N-[[2'-(1-triphenylmethyltetrazol-5yl)biphenyl-4-yl]methyl]-N-valeryl-L-valine methyl ester With methanol; potassium hydroxide for 4h; Heating / reflux; Stage #2: With water for 5h; Heating / reflux;	95%
With sodium hydroxide In methanol for 6h; Reflux;	90%

: C26H32N2O3

: 137862-53-4
N-pentanoyl-N-[[2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]-methyl]-(L)-valine

Conditions

Conditions	Yield
With sodium azide; dichloro[(-)-sparteine-N,N']copper(II) In ethyl acetate at 70 - 80℃; for 4h; Concentration; Reagent/catalyst; Large scale;	92%
With sodium azide; zinc(II) chloride In N,N-dimethyl-formamide at 120 - 130℃;	61%

: 783369-52-8
N-pentanoyl-N-(4-(2-(1-trityl-1H-tetrazol-5-yl)phenyl)phenyl)methyl-L-valine

: 137862-53-4
N-pentanoyl-N-[[2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]-methyl]-(L)-valine

Conditions

Conditions	Yield
With TRILITE SCR-10 gel type In methanol for 6h; Product distribution / selectivity; Reflux;	91%
With sodium hydroxide In methanol at 20℃;	84%

: 1033772-60-9
(2S)-3-methyl-2-{N-[2'-(1H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-N'-(thiophene-2-carbonyl)-amino}-butanoic acid

: 137862-53-4
N-pentanoyl-N-[[2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]-methyl]-(L)-valine

Conditions

Conditions	Yield
With hydrogen; nickel In methanol at 20℃; for 24h;	90%

: potassium N-pentanoyl-N-[{2'-(1-(triphenylmethyl)-1H-tetrazol-5-yl)-1,1'-biphenyl-4-yl}methyl]-L-valinate

A: valsartan

B: 137862-53-4
N-pentanoyl-N-[[2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]-methyl]-(L)-valine

Conditions

Conditions	Yield
Stage #1: potassium N-pentanoyl-N-[{2'-(1-(triphenylmethyl)-1H-tetrazol-5-yl)-1,1'-biphenyl-4-yl}methyl]-L-valinate With methanol for 3h; Heating / reflux; Stage #2: In water; ethyl acetate Stage #3: With hydrogenchloride In water Product distribution / selectivity;	A n/a B 89%

: 2-(tetrazol-5'-yl)phenylboronic acid

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

: 137862-53-4
N-pentanoyl-N-[[2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]-methyl]-(L)-valine

Conditions

Conditions	Yield
Stage #1: 2-(tetrazol-5'-yl)phenylboronic acid; N-(4-iodobenzyl)-N-valeryl-L-valine With sodium hydroxide; tetrakis(triphenylphosphine) palladium(0) In methanol; water for 2.08333h; Heating / reflux; Stage #2: With hydrogenchloride In water pH=1 - 2; Product distribution / selectivity;	88%
Stage #1: 2-(tetrazol-5'-yl)phenylboronic acid; N-(4-iodobenzyl)-N-valeryl-L-valine With sodium hydroxide; bis-triphenylphosphine-palladium(II) chloride In methanol; water at 70℃; for 3h; Stage #2: With hydrogenchloride In water; ethyl acetate pH=1 - 2; Product distribution / selectivity;	85%
Stage #1: 2-(tetrazol-5'-yl)phenylboronic acid; N-(4-iodobenzyl)-N-valeryl-L-valine With sodium methylate; 5%-palladium/activated carbon; triphenylphosphine In methanol at 70℃; for 10h; Stage #2: With hydrogenchloride In water; ethyl acetate pH=3; Product distribution / selectivity;	71.4%

: 3-methyl-2-(N-{[2'-(1H-1,2,3,4-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]methyl}pentanamido)but-2-enoic acid

: 137862-53-4
N-pentanoyl-N-[[2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]-methyl]-(L)-valine

Conditions

Conditions	Yield
With potassium carbonate In 5,5-dimethyl-1,3-cyclohexadiene at 100 - 120℃; for 12h; Temperature; Solvent; Reagent/catalyst;	88%

: sodium N-pentanoyl-N-[{2'-(1-(triphenylmethyl)-1H-tetrazol-5-yl)-1,1'-biphenyl-4-yl}methyl]-L-valinate

A: valsartan

B: 137862-53-4
N-pentanoyl-N-[[2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]-methyl]-(L)-valine

Conditions

Conditions	Yield
Stage #1: sodium N-pentanoyl-N-[{2'-(1-(triphenylmethyl)-1H-tetrazol-5-yl)-1,1'-biphenyl-4-yl}methyl]-L-valinate With methanol Heating / reflux; Stage #2: With sodium hydrogencarbonate In water; ethyl acetate Stage #3: With hydrogenchloride In water Product distribution / selectivity;	A n/a B 82%

: 943019-61-2
N-[4-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)phenyl-4-yl-methyl]-N-pentanoyl-L-valinate

: 143945-72-6
N-trityl-5-(2-bromophenyl)tetrazole

: 137862-53-4
N-pentanoyl-N-[[2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]-methyl]-(L)-valine

Conditions

Conditions	Yield
Stage #1: N-[4-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)phenyl-4-yl-methyl]-N-pentanoyl-L-valinate; N-trityl-5-(2-bromophenyl)tetrazole With potassium phosphate; palladium diacetate; triphenylphosphine In tetrahydrofuran at 60℃; Stage #2: With methanol for 3h; Product distribution / selectivity; Heating / reflux;	77%

: N-(1-oxopentyl)-N-[[2'-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-L-valine barium

: 137862-53-4
N-pentanoyl-N-[[2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]-methyl]-(L)-valine

Conditions

Conditions	Yield
With hydrogenchloride In water; ethyl acetate at 25 - 35℃; Large scale reaction;	77%

: potassium N-pentanoyl-N-[{2'-(1-(triphenylmethyl)-1H-tetrazol-5-yl)-1,1'-biphenyl-4-yl}methyl]-L-valinate

: 137862-53-4
N-pentanoyl-N-[[2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]-methyl]-(L)-valine

Conditions

Conditions	Yield
Stage #1: potassium N-pentanoyl-N-[{2'-(1-(triphenylmethyl)-1H-tetrazol-5-yl)-1,1'-biphenyl-4-yl}methyl]-L-valinate With methanol for 3h; Heating / reflux; Stage #2: With sodium hydrogencarbonate In water Stage #3: With hydrogenchloride In water at 20℃; for 1h; Product distribution / selectivity;	73%
Stage #1: potassium N-pentanoyl-N-[{2'-(1-(triphenylmethyl)-1H-tetrazol-5-yl)-1,1'-biphenyl-4-yl}methyl]-L-valinate With methanol for 3h; Heating / reflux; Stage #2: With sodium hydrogencarbonate In water; ethyl acetate Stage #3: With hydrogenchloride In water Product distribution / selectivity;	66%

: 137863-20-8
(S)-N-(1-benzyloxycarbonyl-2-methyl-prop-1-yl)-N-pentanoyl-N-[2'-(1H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-amine

: 137862-53-4
N-pentanoyl-N-[[2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]-methyl]-(L)-valine

Conditions

Conditions	Yield
With sodium hydroxide In water at 65℃; for 2.5h; optical yield given as %ee;	72.5%
With hydrogen; 5%-palladium/activated carbon In methanol at 20℃; Product distribution / selectivity;	70%
With hydrogen; 5% palladium over charcoal In methanol at 20℃; Product distribution / selectivity;	70%

: benzyl N-{4-[2-(1-benzyl-1H-tetrazole-5-yl)phenyl]benzyl}-N-valeryl-L-valinate

: 137862-53-4
N-pentanoyl-N-[[2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]-methyl]-(L)-valine

Conditions

Conditions	Yield
With 5% palladium on barium sulphate; ammonium formate In water; isopropyl alcohol at 65℃; for 11h;	70.7%

: 3-methyl-(2S)-{pentanoyl-[2'-(1H-tetrazole-5-yl)-biphenyl-4-ylmethyl]-amino}-butyric acid dilithium salt trihydrate

: 137862-53-4
N-pentanoyl-N-[[2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]-methyl]-(L)-valine

Conditions

Conditions	Yield
With hydrogenchloride; water pH=4.0 - 4.2;	70%

: 852212-82-9
(S)-4-isopropyl-3-pentanoyl-2-[2'-(2-trityl-2H-tetrazol-5-yl)-biphenyl-4-yl]oxazolidin-5-one

: 137862-53-4
N-pentanoyl-N-[[2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]-methyl]-(L)-valine

Conditions

Conditions	Yield
Stage #1: (S)-4-isopropyl-3-pentanoyl-2-[2'-(2-trityl-2H-tetrazol-5-yl)-biphenyl-4-yl]oxazolidin-5-one With ammonium formate; 5%-palladium/activated carbon In ISOPROPYLAMIDE at 90℃; Stage #2: With sulfuric acid In tert-butyl methyl ether; ISOPROPYLAMIDE pH=2;	70%
With hydrogen; 5%-palladium/activated carbon In tetrahydrofuran at 60℃; under 3750.38 Torr;	53%

: sodium N-pentanoyl-N-[{2'-(1-(triphenylmethyl)-1H-tetrazol-5-yl)-1,1'-biphenyl-4-yl}methyl]-L-valinate

: 137862-53-4
N-pentanoyl-N-[[2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]-methyl]-(L)-valine

Conditions

Conditions	Yield
Stage #1: sodium N-pentanoyl-N-[{2'-(1-(triphenylmethyl)-1H-tetrazol-5-yl)-1,1'-biphenyl-4-yl}methyl]-L-valinate With methanol Heating / reflux; Stage #2: With sodium hydrogencarbonate In water; ethyl acetate Stage #3: With hydrogenchloride In water Product distribution / selectivity;	70%

: 2-(tetrazol-5'-yl)phenylboronic acid

: 867022-57-9
(S)-2-[(4-bromo-benzyl)-pentanoyl-amino]-3-methyl-butyric acid

: 137862-53-4
N-pentanoyl-N-[[2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]-methyl]-(L)-valine

Conditions

Conditions	Yield
Stage #1: 2-(tetrazol-5'-yl)phenylboronic acid; (S)-2-[(4-bromo-benzyl)-pentanoyl-amino]-3-methyl-butyric acid With sodium hydroxide; 5%-palladium/activated carbon; trisodium tris(3-sulfophenyl)phosphine In water at 70℃; for 2h; Stage #2: With acetic acid In water Product distribution / selectivity;	68%
Stage #1: 2-(tetrazol-5'-yl)phenylboronic acid; (S)-2-[(4-bromo-benzyl)-pentanoyl-amino]-3-methyl-butyric acid With sodium hydroxide; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; ethanol; water for 12.0833h; Heating / reflux; Stage #2: With hydrogenchloride In water pH=1 - 2; Product distribution / selectivity;	60.5%
Stage #1: 2-(tetrazol-5'-yl)phenylboronic acid; (S)-2-[(4-bromo-benzyl)-pentanoyl-amino]-3-methyl-butyric acid With sodium methylate; 5%-palladium/activated carbon; triphenylphosphine In methanol at 70℃; for 10h; Stage #2: With hydrogenchloride In water; ethyl acetate pH=3; Product distribution / selectivity;	58%
Stage #1: 2-(tetrazol-5'-yl)phenylboronic acid; (S)-2-[(4-bromo-benzyl)-pentanoyl-amino]-3-methyl-butyric acid With sodium methylate; triphenylphosphine; palladium dichloride In methanol at 70℃; for 5h; Stage #2: With hydrogenchloride In water; ethyl acetate pH=1 - 2; Product distribution / selectivity;	55.6%

: 137864-44-9
N-[(2'-(1-triphenylmethyl-tetrazol-5-yl)biphenyl-4-yl)methyl]-N-valeroyl-(L)-valine benzyl ester

: 137862-53-4
N-pentanoyl-N-[[2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]-methyl]-(L)-valine

Conditions

Conditions	Yield
Stage #1: N-[(2'-(1-triphenylmethyl-tetrazol-5-yl)biphenyl-4-yl)methyl]-N-valeroyl-(L)-valine benzyl ester In methanol for 8h; Heating / reflux; Stage #2: With hydrogen; palladium on activated charcoal In methanol at 40℃; under 760.051 Torr; for 16h;	67%
With palladium 10% on activated carbon; hydrogen; N-ethyl-N,N-diisopropylamine In methanol under 2250.23 - 3750.38 Torr; for 6h; Autoclave;	110 g
With palladium 10% on activated carbon; hydrogen; N-ethyl-N,N-diisopropylamine In methanol under 2250.23 - 3750.38 Torr; for 6h; Autoclave;	110 g
Multi-step reaction with 2 steps 1.1: methanol; oxalic acid / 1.5 h / 5 - 65 °C 1.2: pH 7.5 2.1: hydrogen / palladium 10% on activated carbon / ethyl acetate / 8 - 10 h / 25 - 30 °C View Scheme

: 137863-90-2
methyl 2-(N-((2'-cyanobiphenyl-4-yl)methyl)pentanamido)-3-methylbutanoate

: 137862-53-4
N-pentanoyl-N-[[2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]-methyl]-(L)-valine

Conditions

Conditions	Yield
Stage #1: methyl 2-(N-((2'-cyanobiphenyl-4-yl)methyl)pentanamido)-3-methylbutanoate With sodium azide; zinc chloride bis(dimethylformamide) complex In N,N-dimethyl-formamide at 130 - 140℃; for 24h; Large scale; Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide at 25 - 30℃; pH=1.5; Large scale; Stage #3: With water; sodium hydroxide In chloroform Large scale;	66.5%
Multi-step reaction with 2 steps 1.1: sodium azide; tri-n-butyltin chloride; tetrabutylammonium bromide / toluene / 72 h / Heating 1.2: 55 percent / acetic acid / toluene; H2O 2.1: 99 percent / NaOH / diethyl ether; H2O / 20 °C View Scheme
Stage #1: methyl 2-(N-((2'-cyanobiphenyl-4-yl)methyl)pentanamido)-3-methylbutanoate With sodium azide; tributyltin chloride In xylene at 25℃; Heating / reflux; Stage #2: With sodium hydroxide In water; xylene at 25 - 35℃; for 24 - 30h; Stage #3: With acetic acid In water pH=7;

: N-(5-(phenyIthio)-1-oxo-pentyI)-N-[[2'-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-L-valine

: 137862-53-4
N-pentanoyl-N-[[2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]-methyl]-(L)-valine

Conditions

Conditions	Yield
Stage #1: N-(5-(phenyIthio)-1-oxo-pentyI)-N-[[2'-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-L-valine With sodium hydroxide; sodium tetrahydroborate; nickel dichloride In methanol; water at 0 - 5℃; for 0.333333h; Stage #2: With acetic acid In water at 25 - 35℃; pH=5.3; Product distribution / selectivity;	46.2%

: C16H15O2N

: 137862-53-4
N-pentanoyl-N-[[2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]-methyl]-(L)-valine

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: 165.9 mg / aq. HCl / 2 h / 50 °C 2.1: molecular sieves 3 Angstroem / tetrahydrofuran / 60 h / 20 °C 2.2: 90 percent / sodium cyanoborohydride / tetrahydrofuran; ethanol / 24 h / 23 °C 3.1: 98 percent / pyridine / CH2Cl2 / 2 h / 40 °C 4.1: sodium azide; tri-n-butyltin chloride; tetrabutylammonium bromide / toluene / 72 h / Heating 4.2: 55 percent / acetic acid / toluene; H2O 5.1: 99 percent / NaOH / diethyl ether; H2O / 20 °C View Scheme

Yield

Multi-step reaction with 5 steps
1.1: 165.9 mg / aq. HCl / 2 h / 50 °C
2.1: molecular sieves 3 Angstroem / tetrahydrofuran / 60 h / 20 °C
2.2: 90 percent / sodium cyanoborohydride / tetrahydrofuran; ethanol / 24 h / 23 °C
3.1: 98 percent / pyridine / CH2Cl2 / 2 h / 40 °C
4.1: sodium azide; tri-n-butyltin chloride; tetrabutylammonium bromide / toluene / 72 h / Heating
4.2: 55 percent / acetic acid / toluene; H2O
5.1: 99 percent / NaOH / diethyl ether; H2O / 20 °C
View Scheme

: 137863-89-9
N-[(2'-cyanobiphenyl-4-yl)-methyl]-(L)-valine methyl ester

: 137862-53-4
N-pentanoyl-N-[[2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]-methyl]-(L)-valine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 98 percent / pyridine / CH2Cl2 / 2 h / 40 °C 2.1: sodium azide; tri-n-butyltin chloride; tetrabutylammonium bromide / toluene / 72 h / Heating 2.2: 55 percent / acetic acid / toluene; H2O 3.1: 99 percent / NaOH / diethyl ether; H2O / 20 °C View Scheme
Multi-step reaction with 3 steps 1.1: 2,6-dimethylpyridine / toluene / 2 h / 5 - 30 °C 2.1: sodium azide / toluene / 50 h / Reflux 3.1: sodium hydroxide; water / toluene / 12 h / 20 - 30 °C 3.2: pH 1 - 2.5 View Scheme
Multi-step reaction with 3 steps 1: 2,6-dimethylpyridine / water; toluene / 2 h / 5 - 30 °C 2: sodium azide / toluene / 50 h / Reflux 3: sodium hydroxide; water / toluene / 12 h / 20 - 30 °C View Scheme

: 400747-06-0
C16H13O2N

: 137862-53-4
N-pentanoyl-N-[[2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]-methyl]-(L)-valine

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: 167.9 mg / aq. HCl / 2 h / 50 °C 2.1: molecular sieves 3 Angstroem / tetrahydrofuran / 60 h / 20 °C 2.2: 90 percent / sodium cyanoborohydride / tetrahydrofuran; ethanol / 24 h / 23 °C 3.1: 98 percent / pyridine / CH2Cl2 / 2 h / 40 °C 4.1: sodium azide; tri-n-butyltin chloride; tetrabutylammonium bromide / toluene / 72 h / Heating 4.2: 55 percent / acetic acid / toluene; H2O 5.1: 99 percent / NaOH / diethyl ether; H2O / 20 °C View Scheme

Yield

Multi-step reaction with 5 steps
1.1: 167.9 mg / aq. HCl / 2 h / 50 °C
2.1: molecular sieves 3 Angstroem / tetrahydrofuran / 60 h / 20 °C
2.2: 90 percent / sodium cyanoborohydride / tetrahydrofuran; ethanol / 24 h / 23 °C
3.1: 98 percent / pyridine / CH2Cl2 / 2 h / 40 °C
4.1: sodium azide; tri-n-butyltin chloride; tetrabutylammonium bromide / toluene / 72 h / Heating
4.2: 55 percent / acetic acid / toluene; H2O
5.1: 99 percent / NaOH / diethyl ether; H2O / 20 °C
View Scheme

: 10602-01-4
p-bromobenzaldehyde 1,3-dioxolane

: 137862-53-4
N-pentanoyl-N-[[2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]-methyl]-(L)-valine

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: copper(II) oxide; potassium carbonate; potassium fluoride / palladium(II) bromide; 1,10-phenanthroline / quinoline / 24 h / 170 °C 2.1: 167.9 mg / aq. HCl / 2 h / 50 °C 3.1: molecular sieves 3 Angstroem / tetrahydrofuran / 60 h / 20 °C 3.2: 90 percent / sodium cyanoborohydride / tetrahydrofuran; ethanol / 24 h / 23 °C 4.1: 98 percent / pyridine / CH2Cl2 / 2 h / 40 °C 5.1: sodium azide; tri-n-butyltin chloride; tetrabutylammonium bromide / toluene / 72 h / Heating 5.2: 55 percent / acetic acid / toluene; H2O 6.1: 99 percent / NaOH / diethyl ether; H2O / 20 °C View Scheme

Yield

Multi-step reaction with 6 steps
1.1: copper(II) oxide; potassium carbonate; potassium fluoride / palladium(II) bromide; 1,10-phenanthroline / quinoline / 24 h / 170 °C
2.1: 167.9 mg / aq. HCl / 2 h / 50 °C
3.1: molecular sieves 3 Angstroem / tetrahydrofuran / 60 h / 20 °C
3.2: 90 percent / sodium cyanoborohydride / tetrahydrofuran; ethanol / 24 h / 23 °C
4.1: 98 percent / pyridine / CH2Cl2 / 2 h / 40 °C
5.1: sodium azide; tri-n-butyltin chloride; tetrabutylammonium bromide / toluene / 72 h / Heating
5.2: 55 percent / acetic acid / toluene; H2O
6.1: 99 percent / NaOH / diethyl ether; H2O / 20 °C
View Scheme

: 3839-22-3
2-cyanobenzoic acid

: 137862-53-4
N-pentanoyl-N-[[2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]-methyl]-(L)-valine

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: 50 percent / basic copper(II) carbonate; potassium carbonate; triphenylphosphine / palladium(II) bromide; 1,10-phenanthroline / quinoline / 24 h / 170 °C 2.1: molecular sieves 3 Angstroem / tetrahydrofuran / 60 h / 20 °C 2.2: 90 percent / sodium cyanoborohydride / tetrahydrofuran; ethanol / 24 h / 23 °C 3.1: 98 percent / pyridine / CH2Cl2 / 2 h / 40 °C 4.1: sodium azide; tri-n-butyltin chloride; tetrabutylammonium bromide / toluene / 72 h / Heating 4.2: 55 percent / acetic acid / toluene; H2O 5.1: 99 percent / NaOH / diethyl ether; H2O / 20 °C View Scheme
Multi-step reaction with 6 steps 1.1: copper(II) oxide; potassium carbonate; potassium fluoride / palladium(II) bromide; 1,10-phenanthroline / quinoline / 24 h / 170 °C 2.1: 167.9 mg / aq. HCl / 2 h / 50 °C 3.1: molecular sieves 3 Angstroem / tetrahydrofuran / 60 h / 20 °C 3.2: 90 percent / sodium cyanoborohydride / tetrahydrofuran; ethanol / 24 h / 23 °C 4.1: 98 percent / pyridine / CH2Cl2 / 2 h / 40 °C 5.1: sodium azide; tri-n-butyltin chloride; tetrabutylammonium bromide / toluene / 72 h / Heating 5.2: 55 percent / acetic acid / toluene; H2O 6.1: 99 percent / NaOH / diethyl ether; H2O / 20 °C View Scheme
Multi-step reaction with 6 steps 1.1: copper(II) oxide; potassium carbonate; potassium fluoride / palladium(II) bromide; 1,10-phenanthroline / quinoline / 24 h / 170 °C 2.1: 165.9 mg / aq. HCl / 2 h / 50 °C 3.1: molecular sieves 3 Angstroem / tetrahydrofuran / 60 h / 20 °C 3.2: 90 percent / sodium cyanoborohydride / tetrahydrofuran; ethanol / 24 h / 23 °C 4.1: 98 percent / pyridine / CH2Cl2 / 2 h / 40 °C 5.1: sodium azide; tri-n-butyltin chloride; tetrabutylammonium bromide / toluene / 72 h / Heating 5.2: 55 percent / acetic acid / toluene; H2O 6.1: 99 percent / NaOH / diethyl ether; H2O / 20 °C View Scheme

: 131-63-5
ammonium 2-(aminocarbonyl)benzoate

: 137862-53-4
N-pentanoyl-N-[[2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]-methyl]-(L)-valine

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: 72 percent / acetic anhydride; pyridine 2.1: 50 percent / basic copper(II) carbonate; potassium carbonate; triphenylphosphine / palladium(II) bromide; 1,10-phenanthroline / quinoline / 24 h / 170 °C 3.1: molecular sieves 3 Angstroem / tetrahydrofuran / 60 h / 20 °C 3.2: 90 percent / sodium cyanoborohydride / tetrahydrofuran; ethanol / 24 h / 23 °C 4.1: 98 percent / pyridine / CH2Cl2 / 2 h / 40 °C 5.1: sodium azide; tri-n-butyltin chloride; tetrabutylammonium bromide / toluene / 72 h / Heating 5.2: 55 percent / acetic acid / toluene; H2O 6.1: 99 percent / NaOH / diethyl ether; H2O / 20 °C View Scheme
Multi-step reaction with 7 steps 1.1: 72 percent / acetic anhydride; pyridine 2.1: copper(II) oxide; potassium carbonate; potassium fluoride / palladium(II) bromide; 1,10-phenanthroline / quinoline / 24 h / 170 °C 3.1: 167.9 mg / aq. HCl / 2 h / 50 °C 4.1: molecular sieves 3 Angstroem / tetrahydrofuran / 60 h / 20 °C 4.2: 90 percent / sodium cyanoborohydride / tetrahydrofuran; ethanol / 24 h / 23 °C 5.1: 98 percent / pyridine / CH2Cl2 / 2 h / 40 °C 6.1: sodium azide; tri-n-butyltin chloride; tetrabutylammonium bromide / toluene / 72 h / Heating 6.2: 55 percent / acetic acid / toluene; H2O 7.1: 99 percent / NaOH / diethyl ether; H2O / 20 °C View Scheme
Multi-step reaction with 7 steps 1.1: 72 percent / acetic anhydride; pyridine 2.1: copper(II) oxide; potassium carbonate; potassium fluoride / palladium(II) bromide; 1,10-phenanthroline / quinoline / 24 h / 170 °C 3.1: 165.9 mg / aq. HCl / 2 h / 50 °C 4.1: molecular sieves 3 Angstroem / tetrahydrofuran / 60 h / 20 °C 4.2: 90 percent / sodium cyanoborohydride / tetrahydrofuran; ethanol / 24 h / 23 °C 5.1: 98 percent / pyridine / CH2Cl2 / 2 h / 40 °C 6.1: sodium azide; tri-n-butyltin chloride; tetrabutylammonium bromide / toluene / 72 h / Heating 6.2: 55 percent / acetic acid / toluene; H2O 7.1: 99 percent / NaOH / diethyl ether; H2O / 20 °C View Scheme

: 638-29-9
n-valeryl chloride

: 137862-53-4
N-pentanoyl-N-[[2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]-methyl]-(L)-valine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 98 percent / pyridine / CH2Cl2 / 2 h / 40 °C 2.1: sodium azide; tri-n-butyltin chloride; tetrabutylammonium bromide / toluene / 72 h / Heating 2.2: 55 percent / acetic acid / toluene; H2O 3.1: 99 percent / NaOH / diethyl ether; H2O / 20 °C View Scheme
Multi-step reaction with 3 steps 1.1: potassium carbonate / dichloromethane / 5.5 h / 0 - 5 °C 2.1: sodium azide; zinc(II) chloride / diethylene glycol dimethyl ether / 26 h / 120 °C 3.1: sodium hydroxide / water / 4 h / 40 °C 3.2: pH 1.5 - 2 / Cooling; Acidic conditions View Scheme
Multi-step reaction with 3 steps 1.1: potassium carbonate / dichloromethane / 5.5 h / 0 - 5 °C 2.1: sodium azide; zinc(II) chloride / diethylene glycol dimethyl ether / 24 h / 120 °C 3.1: sodium hydroxide / water / 4 h / 40 °C 3.2: pH 1.5 - 2 / Cooling; Acidic conditions View Scheme

: 76-83-5
trityl chloride

: 121-44-8
triethylamine

: 137862-53-4
N-pentanoyl-N-[[2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]-methyl]-(L)-valine

: triethylammonium N-pentanoyl-N-[{2'-(1-(triphenylmethyl)-1H-tetrazol-5-yl)-1,1'-biphenyl-4-yl}methyl]-L-valinate

Conditions

Conditions	Yield
In tetrahydrofuran at 20℃; for 5h; Product distribution / selectivity;	100%

...Expand

: 137862-53-4
N-pentanoyl-N-[[2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]-methyl]-(L)-valine

: C24H28(3)HN5O3

Conditions

Conditions	Yield
With tritium; η4-cycloocta-1,5-diene(1,3-dimesitylimidazoline-2-ylidene)(triphenylphosphine)iridium(I) tetrakis[(3,5-trifluoromethylphenyl)]borate; caesium carbonate In methanol at 20 - 50℃; for 3.25h;	98.9%

: 137862-53-4
N-pentanoyl-N-[[2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]-methyl]-(L)-valine

: magnesium-valsartan-hexahydrate

Conditions

Conditions	Yield
With water; magnesium oxide In ethanol at 20 - 40℃; pH=4 - 7.5;	95%

: 4-(((2S,4R)-1-([1,1'-biphenyl]-4-yl)-5-ethoxy-4-methyl-5-oxopentan-2-yl)amino)-4-oxobutanoic acid

: 137862-53-4
N-pentanoyl-N-[[2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]-methyl]-(L)-valine

: trisodium [3-((1S,3R)-1-biphenyl-4-ylmethyl-3-ethoxycarbonyl-1-butylcarbamoyl)propionate-(S)-3’-methyl-2’-(pentanoyl{2”-(tetrazol-5-ylate)biphenyl-4’-ylmethyl}amino)butyrate]hemipentahydrate

Conditions

Conditions	Yield
With sodium hydroxide In methanol; water at 15 - 35℃; for 1h; Solvent; Temperature;	94.23%

: 108-01-0
2-(N,N-dimethylamino)ethanol

: 137862-53-4
N-pentanoyl-N-[[2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]-methyl]-(L)-valine

: C28H38N6O3

Conditions

Conditions	Yield
With thionyl chloride In dichloromethane for 1h; Reflux;	93.1%

: 100-37-8
2-(Diethylamino)ethanol

: 137862-53-4
N-pentanoyl-N-[[2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]-methyl]-(L)-valine

: C30H42N6O3

Conditions

Conditions	Yield
With thionyl chloride In dichloromethane for 1h; Reflux;	92.5%

: N-(3-carboxyl-1-oxopropyl)-(4S)-(p-phenylphenyl-methyl)-4-amino-(2R)-methylbutanoic acid ethyl ester calcium salt

: 137862-53-4
N-pentanoyl-N-[[2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]-methyl]-(L)-valine

: 936623-90-4
trisodium [3-((1S,3R)-1-biphenyl-4-yl-methyl-3-ethoxycarbonyl-1-butylcarbamoyl)propionate-(S)-3’-methyl-2’-(pentanoyl{2”-(tetrazol-5-ylate)biphenyl-4’-yl-methyl}amino)butyrate] hemipentahydrate

Conditions

Conditions	Yield
Stage #1: N-(3-carboxyl-1-oxopropyl)-(4S)-(p-phenylphenyl-methyl)-4-amino-(2R)-methylbutanoic acid ethyl ester calcium salt With hydrogenchloride; water In Isopropyl acetate Stage #2: N-pentanoyl-N-[[2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]-methyl]-(L)-valine With sodium hydroxide In n-heptane; water; acetone at 45℃; Temperature;	91.9%

: 137862-53-4
N-pentanoyl-N-[[2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]-methyl]-(L)-valine

: (S)-N-(1-carboxy-2-methyl-prop-1-yl)-N-pentanoyl-N-[2'-(1H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-amine disodium salt

Conditions

Conditions	Yield
With sodium hydroxide In water; acetone at 25 - 35℃; for 5h;	91.66%
With sodium carbonate In water; acetone for 3h; Reflux;
With sodium hydroxide In ethanol

: 149690-05-1
α-ethyl (αR,γS)-γ-<(3-carboxy-1-oxopropyl)amino>-α-methyl<1,1'-biphenyl>-4-pentanoate monosodium salt

: 137862-53-4
N-pentanoyl-N-[[2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]-methyl]-(L)-valine

: trisodium [3-((1S,3R)-1-biphenyl-4-ylmethyl-3-ethoxycarbonyl-1-butylcarbamoyl)propionate-(S)-3’-methyl-2’-(pentanoyl{2”-(tetrazol-5-ylate)biphenyl-4’-ylmethyl}amino)butyrate]hemipentahydrate

Conditions

Conditions	Yield
With sodium hydroxide In Isopropyl acetate; water; acetonitrile at 40 - 65℃;	91%
Stage #1: N-pentanoyl-N-[[2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]-methyl]-(L)-valine With sodium hydroxide In methanol at 25 - 35℃; for 0.5h; Stage #2: α-ethyl (αR,γS)-γ-<(3-carboxy-1-oxopropyl)amino>-α-methyl<1,1'-biphenyl>-4-pentanoate monosodium salt In acetone at 25 - 35℃; for 0.166667h; Solvent;	6.3 g

: (2R,4S)-5-(biphenyl-4-yl)-4-[(3-carboxypropionyl)amino]-2-methylpentanoic acid ethyl ester dicyclohexylamine salt

: 137862-53-4
N-pentanoyl-N-[[2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]-methyl]-(L)-valine

: LCZ696

Conditions

Conditions	Yield
With sodium hydroxide In Isopropyl acetate; water; acetone at 25 - 55℃; for 4.5h; Solvent; Temperature;	91%

: 4-(((2S,4R)-1-([1,1'-biphenyl]-4-yl)-5-ethoxy-4-methyl-5-oxopentan-2-yl)amino)-4-oxobutanoic acid

: 137862-53-4
N-pentanoyl-N-[[2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]-methyl]-(L)-valine

: 936623-90-4
trisodium [3-((1S,3R)-1-biphenyl-4-yl-methyl-3-ethoxycarbonyl-1-butylcarbamoyl)propionate-(S)-3’-methyl-2’-(pentanoyl{2”-(tetrazol-5-ylate)biphenyl-4’-yl-methyl}amino)butyrate] hemipentahydrate

Conditions

Conditions	Yield
With sodium hydroxide In water; acetone at 25 - 35℃; for 1h;	90.83%

: 137862-53-4
N-pentanoyl-N-[[2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]-methyl]-(L)-valine

: C24H28(2)HN5O3

Conditions

Conditions	Yield
With η4-cycloocta-1,5-diene(1,3-dimesitylimidazoline-2-ylidene)(triphenylphosphine)iridium(I) tetrakis[(3,5-trifluoromethylphenyl)]borate; water-d2; caesium carbonate In methanol at 50℃; for 6h;	88%

: C24H30N2O5

: 137862-53-4
N-pentanoyl-N-[[2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]-methyl]-(L)-valine

: C47H54N7O8(2-)*3Na(1+)*2.5H2O

Conditions

Conditions	Yield
With water; sodium hydroxide In acetone at 20℃; for 2h;	87%

: C26H34N2O5

: 137862-53-4
N-pentanoyl-N-[[2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]-methyl]-(L)-valine

: C49H58N7O8(2-)*3Na(1+)*2.5H2O

Conditions

Conditions	Yield
With water; sodium hydroxide In acetone for 2h;	85.6%

: 3C24H28NO5(1-)*3Na(1+)*C24H29NO5*2C2H4O2

: 7732-18-5
water

: 137862-53-4
N-pentanoyl-N-[[2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]-methyl]-(L)-valine

: C24H28NO5(1-)*C24H28N5O3(1-)*2Na(1+)*2.5H2O

Conditions

Conditions	Yield
With sodium hydroxide In Isopropyl acetate; acetone at 40 - 45℃; for 2h;	85%

...Expand

: C28H38N2O5

: 137862-53-4
N-pentanoyl-N-[[2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]-methyl]-(L)-valine

: C51H62N7O8(2-)*3Na(1+)*2.5H2O

Conditions

Conditions	Yield
With water; sodium hydroxide In acetone for 2h;	84.2%

: 67-56-1
methanol

: 137862-53-4
N-pentanoyl-N-[[2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]-methyl]-(L)-valine

: 137863-17-3
methyl N-((2’-(1H-tetrazol-5-yl)-[1,1’-biphenyl]-4-yl)methyl)-N-pentanoyl-L-valinate

Conditions

Conditions	Yield
With thionyl chloride at 0 - 25℃; for 4.5h;	83%
With thionyl chloride at 4 - 20℃; for 3h;

: C30H42N2O5

: 137862-53-4
N-pentanoyl-N-[[2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]-methyl]-(L)-valine

: C53H66N7O8(2-)*3Na(1+)*2.5H2O

Conditions

Conditions	Yield
With water; sodium hydroxide In acetone for 3.5h;	82.2%

: (2R,4S)-5-biphenyl-4-yl-4-(3-carboxypropionylamino)-2-methylpentanoic acid ethyl ester 1-(naphthalen-1-yl)ethan-1-amine salt

: 137862-53-4
N-pentanoyl-N-[[2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]-methyl]-(L)-valine

: trisodium [3-((1S,3R)-1-biphenyl-4-ylmethyl-3-ethoxycarbonyl-1-butylcarbamoyl)propionate-(S)-3’-methyl-2’-(pentanoyl{2”-(tetrazol-5-ylate)biphenyl-4’-ylmethyl}amino)butyrate]hemipentahydrate

Conditions

Conditions	Yield
Stage #1: (2R,4S)-5-biphenyl-4-yl-4-(3-carboxypropionylamino)-2-methylpentanoic acid ethyl ester 1-(naphthalen-1-yl)ethan-1-amine salt; N-pentanoyl-N-[[2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]-methyl]-(L)-valine In acetone at 10℃; Stage #2: With sodium hydroxide In water; acetone	80%

Valsartan Chemical Properties

Structure of Valsartan (CAS NO.137862-53-4):

IUPAC Name: (2S)-3-Methyl-2-[pentanoyl-[[4-[2-(2H-tetrazol-5-yl)phenyl]phenyl]methyl]amino]butanoic acid
Molecular Formula: C₂₄H₂₉N₅O₃
Molar mass: 435.5188 g/mol
Density: 1.212 g/cm³
Flash Point: 368 °C
Index of Refraction: 1.586
Boiling Point: 684.9 °C at 760 mmHg
Vapour Pressure: 1.06E-19 mmHg at 25 °C
Melting Point: 116-117 °C
Appearance: white crystalline powder
XLogP3-AA: 4.4
H-Bond Donor: 2
H-Bond Acceptor: 6
Rotatable Bond Count: 10
Tautomer Count: 2
Exact Mass: 435.22704
MonoIsotopic Mass: 435.22704
Topological Polar Surface Area: 112
Heavy Atom Count: 32
Canonical SMILES: CCCCC(=O)N(CC1=CC=C(C=C1)C2=CC=CC=C2C3=NNN=N3)C(C(C)C)C(=O)O
Isomeric SMILES: CCCCC(=O)N(CC1=CC=C(C=C1)C2=CC=CC=C2C3=NNN=N3)[C@@H](C(C)C)C(=O)O
InChI: InChI=1S/C24H29N5O3/c1-4-5-10-21(30)29(22(16(2)3)24(31)32)15-17-11-13-18(14-12-17)19-8-6-7-9-20(19)23-25-27-28-26-23/h6-9,11-14,16,22H,4-5,10,15H2,1-3H3,(H,31,32)(H,25,26,27,28)/t22-/m0/s1
InChIKey: ACWBQPMHZXGDFX-QFIPXVFZSA-N
Product Categories: Active Pharmaceutical Ingredients; Antihypertensive; APIs; Intermediates & Fine Chemicals; Pharmaceuticals; API's

Valsartan Uses

Valsartan (CAS NO.137862-53-4) is indicated for treatment of high blood pressure, congestive heart failure (CHF), or post-myocardial infarction (MI) in the U.S.. A study released by the Journal of Clinical Investigation in 2007 found some efficacy in the use of valsartan in the treatment and prevention of Alzheimer's Disease although such use is considered to be highly experimental.

Valsartan Safety Profile

Hazard Codes: Irritant Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S37/39:Wear suitable gloves and eye/face protection.

Valsartan Specification

Valsartan (CAS NO.137862-53-4) is also named as CGP 48933 ; Diovan ; HSDB 7519 ; UNII-80M03YXJ7I ; Valtan ; Valzaar ; L-Valine, N-(1-oxopentyl)-N-((2'-(1H-tetrazol-5-yl)(1,1'-biphenyl)-4-yl)methyl)- ; N-(p-(o-1H-Tetrazol-5-ylphenyl)benzyl)-N-valeryl-L-valine . It is an angiotensin II receptor antagonist (more commonly called an "ARB", which stands for angiotensin receptor blocker), with particularly high affinity for the type I (AT₁) angiotensin receptor.

Product Name

Valsartan

Synthetic route

Valsartan Chemical Properties

Valsartan Uses

Valsartan Safety Profile

Valsartan Specification

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