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Valsartan
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Name

Valsartan

 EINECS 1592732-453-0
CAS No. 137862-53-4 Density 1.212 g/cm3
PSA 112.07000 LogP 4.16170
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 N/A Appearance white crystalline powder
Safety 26-37/39 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 137862-53-4 (Valsartan) Hazard Symbols IrritantXi
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;

Article Data 68

Valsartan 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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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%

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: IrritantXi
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.

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