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Losartan
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Name

Losartan

 EINECS 601-329-8
CAS No. 114798-26-4 Density 1.35 g/cm3
PSA 92.51000 LogP 4.26680
Solubility 4.8mg/L at 20℃ Melting Point 183-184 °C
Formula C22H23ClN6O Boiling Point 682 °C at 760mmHg
Molecular Weight 422.917 Flash Point 366.3 °C
Transport Information N/A Appearance pale yellow solid
Safety 26-36 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 114798-26-4 (Losartan) Hazard Symbols IrritantXi
Synonyms

2-n-butyl-4-chloro-5-hydroxymethyl-1-[[2-(1H-tetrazol-5-yl)-biphenyl-4-yl]methyl]imidazole;DUP 89;1H-imidazole-5-methanol, 2-butyl-4-chloro-1-[[2-(2H-tetrazol-5-yl)[1,1-biphenyl]-4-yl]methyl]-;[2-butyl-5-chloro-3-[[4-[2-(2H-tetrazol-5-yl)phenyl]phenyl]methyl]imidazol-4-yl]methanol;2-butyl-4-chloro-1-[p-(o-1H-tetrazol-5ylphenyl)benzyl]imidazole-5-methanol;2-Butyl-4-chloro-1-[[2-(1H-tetrazol-5-yl)[1,1-biphenyl]-4-yl]methyl-1H-imidazole-5-methanol;Losartan Base;

Article Data 55

Losartan Synthetic route

114772-55-3

2-n-Butyl-4-chloro-1-[(2'-cyanobiphenyl-4-yl)-methyl]-5-(hydroxymethyl)imidazole

114798-26-4

lorsartan

Conditions
ConditionsYield
With sodium azide In 1-methyl-pyrrolidin-2-one99%
With sodium azide In toluene at 20℃;95%
With sodium azide; zinc trifluoromethanesulfonate In water at 100℃; for 6h; Solvent; Temperature; Time; Green chemistry;91%
67-56-1

methanol

124751-00-4

2-Butyl-4-chloro-1-[[2'-[1-(triphenylmethyl)-1H-tetrazol-5-yl][1,1'-biphenyl]-4-yl]methyl]-1H-imidazole-5-methanol

A

596-31-6

methoxytriphenylmethane

B

114798-26-4

lorsartan

Conditions
ConditionsYield
for 7h; Heating / reflux;A 90%
B 98%

1-{[2′-(1-benzyl-1H-tetrazol-5-yl)-1,1′-biphenyl-4-yl]methyl}-2-butyl-4-chloro-1H-imidazole-5-carbaldehyde

114798-26-4

lorsartan

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen at 20℃; under 760.051 Torr; for 24h;97%
With palladium on carbon; hydrogen; acetic acid at 20℃; for 12h;94%
Multi-step reaction with 2 steps
1: sodium tetrahydroborate / methanol; toluene / 0.5 h / 25 °C / Inert atmosphere
2: ammonium formate; 5% palladium on barium sulphate / isopropyl alcohol; water / 8 h / 25 - 60 °C
View Scheme
Multi-step reaction with 2 steps
1: sodium tetrahydroborate; methanol / toluene / 0.58 h / 0 - 25 °C
2: 5% palladium on barium sulphate; ammonium formate / water; isopropyl alcohol / 8 h / 60 °C
View Scheme
124751-00-4

2-Butyl-4-chloro-1-[[2'-[1-(triphenylmethyl)-1H-tetrazol-5-yl][1,1'-biphenyl]-4-yl]methyl]-1H-imidazole-5-methanol

A

596-31-6

methoxytriphenylmethane

B

114798-26-4

lorsartan

Conditions
ConditionsYield
Stage #1: 2-Butyl-4-chloro-1-[[2'-[1-(triphenylmethyl)-1H-tetrazol-5-yl][1,1'-biphenyl]-4-yl]methyl]-1H-imidazole-5-methanol With hydroxylamine hydrochloride In methanol; water; acetone at 20℃; for 2h;
Stage #2: With sodium hydroxide In methanol; water; acetone at 20 - 25℃; pH=3.8 - 4.2;		A n/a
B 95%
Stage #1: 2-Butyl-4-chloro-1-[[2'-[1-(triphenylmethyl)-1H-tetrazol-5-yl][1,1'-biphenyl]-4-yl]methyl]-1H-imidazole-5-methanol With hydrogenchloride In methanol; water; acetone at 20℃; for 2h;
Stage #2: With sodium hydroxide In methanol; water; acetone at 20 - 25℃; pH=3.8 - 4.2;		A n/a
B 93%
Stage #1: 2-Butyl-4-chloro-1-[[2'-[1-(triphenylmethyl)-1H-tetrazol-5-yl][1,1'-biphenyl]-4-yl]methyl]-1H-imidazole-5-methanol With sulfuric acid In methanol; water; acetone at 20℃; for 2h;
Stage #2: With sodium hydroxide In methanol; water; acetone at 20 - 25℃; pH=3.8 - 4.2;		A n/a
B 91.3%
141-78-6

ethyl acetate

A

C24H25ClN6O2

B

596-31-6

methoxytriphenylmethane

C

114798-26-4

lorsartan

Conditions
ConditionsYield
Stage #1: 2-Butyl-4-chloro-1-[[2'-[1-(triphenylmethyl)-1H-tetrazol-5-yl][1,1'-biphenyl]-4-yl]methyl]-1H-imidazole-5-methanol With hydroxylamine hydrochloride In methanol; water; acetone at 20℃; for 2h;
Stage #2: With sodium hydroxide In methanol; water; acetone at 20 - 25℃; pH=3.8 - 4.2;
Stage #3: ethyl acetate at 40℃; for 1h;		A n/a
B n/a
C 95%
124751-00-4

2-Butyl-4-chloro-1-[[2'-[1-(triphenylmethyl)-1H-tetrazol-5-yl][1,1'-biphenyl]-4-yl]methyl]-1H-imidazole-5-methanol

114798-26-4

lorsartan

Conditions
ConditionsYield
Stage #1: 2-Butyl-4-chloro-1-[[2'-[1-(triphenylmethyl)-1H-tetrazol-5-yl][1,1'-biphenyl]-4-yl]methyl]-1H-imidazole-5-methanol; hydroxylamine hydrochloride In methanol at 60℃; for 2.5h; pH=2.95;
Stage #2: With triethylamine In methanol at 0 - 40℃; for 1h; pH=3.6; Product distribution / selectivity;		94.7%
Stage #1: 2-Butyl-4-chloro-1-[[2'-[1-(triphenylmethyl)-1H-tetrazol-5-yl][1,1'-biphenyl]-4-yl]methyl]-1H-imidazole-5-methanol; hydroxyammonium sulfate In isopropyl alcohol at 60 - 65℃; for 4h; pH=2.4;
Stage #2: With triethylamine In isopropyl alcohol at 0 - 5℃; for 2h; pH=3.5; Product distribution / selectivity;		93.8%
With hydrogenchloride; water In tetrahydrofuran at 20℃; for 4h;90%

2-n-butyl-4-chloro-5-hydroxymethyl-1-[[2'-(1H-tetrazole-5-yl)[1,1'-biphenyl]-4-yl]]-1H-imidazole sodium salt

114798-26-4

lorsartan

Conditions
ConditionsYield
With sulfuric acid In water; ethyl acetate at 10 - 25℃; for 1h; pH=3.6 - 3.8; Purification / work up;94%
124750-99-8

cozaar

114798-26-4

lorsartan

Conditions
ConditionsYield
With sulfuric acid In water; ethyl acetate at 10 - 25℃; for 1h; pH=3.6 - 3.8; Purification / work up;93%
With hydrogenchloride In tetrahydrofuran; water; chlorobenzene86.8%
With hydrogenchloride In tetrahydrofuran; water; chlorobenzene pH=3.5 - 3.6;84%
With hydrogenchloride In tetrahydrofuran; water; chlorobenzene pH=3.5 - 3.6;42.6 g

2-n-butyl-4-chloro-1-[[2'-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-1H-imidazole-5-methanol p-toluenesulfonate

114798-26-4

lorsartan

Conditions
ConditionsYield
With potassium hydroxide In water; acetonitrile at 15 - 25℃; pH=3.5 - 3.6;93%
133909-99-6

2-n-butyl-4-chloro-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl]-1H-imidazole-5-methanol

114798-26-4

lorsartan

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran at 25℃; for 4h;89%

Losartan Specification

Losartan, with its IUPAC Name of [2-Butyl-5-chloro-3-[[4-[2-(2H-tetrazol-5-yl)phenyl]phenyl]methyl]imidazol-4-yl]methanol, is one kind of pale yellow solid. And it belongs to the Classification Code which include Angiotensin II Type 1 Receptor Blockers; Anti-arrhythmia agents; Antihypertensive agents; Cardiovascular Agents; Drug / Therapeutic Agent; Human Data. Losartan is used mainly to treat high blood pressure (hypertension). Losartan is being researched as a possible drug for marked slowing of aortic enlargement in Marfan and related syndromes.

Physical properties about Losartan are: (1)ACD/LogP: 4.364; (2)ACD/LogD (pH 5.5): 3.13; (3)ACD/LogD (pH 7.4): 2.39; (4)ACD/BCF (pH 5.5): 71.72; (5)ACD/BCF (pH 7.4): 13.05; (6)ACD/KOC (pH 5.5): 331.15; (7)ACD/KOC (pH 7.4): 60.25; (8)#H bond acceptors: 7; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 9; (11)Index of Refraction: 1.681; (12)Molar Refractivity: 118.236 cm3; (13)Molar Volume: 312.526 cm3; (14)Polarizability: 46.872 10-24cm3; (15)Surface Tension: 53.3219985961914 dyne/cm; (16)Density: 1.353 g/cm3; (17)Flash Point: 366.27 °C; (18)Enthalpy of Vaporization: 105.096 kJ/mol; (19)Boiling Point: 682.016 °C at 760 mmHg

Production of Losartan: Losartan could be produced through the following simple way:

You can still convert the following datas into molecular structure:
1). InChI: InChI=1S/C22H23ClN6O/c1-2-3-8-20-24-21(23)19(14-30)29(20)13-15-9-11-16(12-10-15)17-6-4-5-7-18(17)22-25-27-28-26-22/h4-7,9-12,30H,2-3,8,13-14H2,1H3,(H,25,26,27,28)
2). InChIKey: InChIKey=PSIFNNKUMBGKDQ-UHFFFAOYSA-N
3). Smiles: n1(c(nc(c1CO)Cl)CCCC)Cc1ccc(c2c(c3nnn[nH]3)cccc2)cc1

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