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Olmesartan medoxomil
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Name

Olmesartan medoxomil

 EINECS 604-433-1
CAS No. 144689-63-4 Density 1.38 g/cm3
PSA 162.16000 LogP 4.17000
Solubility N/A Melting Point 180 °C
Formula C29H30N6O6 Boiling Point 804.2 °C at 760 mmHg
Molecular Weight 558.594 Flash Point 440.2 °C
Transport Information N/A Appearance White to off-white crystalline powder
Safety Risk Codes R36/38; R41; R38
Molecular Structure Molecular Structure of 144689-63-4 (Olmesartan medoxomil) Hazard Symbols Xi
Synonyms

Olmetec (TN);Cs 866;Benicar (TN);Benicar;Olmetec;1H-Imidazole-5-carboxylic acid,4-(1-hydroxy-1-methylethyl)-2-propyl- 1-[[2'-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]- methyl]-,(5-methyl-2-oxo-1,3-dioxol-4-yl)- methyl ester;(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 5-(2-hydroxypropan-2-yl)-2-propyl-3-[[4-[2-(2H-tetrazol-5-yl)phenyl]phenyl]methyl]imidazole-4-carboxylate;4-(1-hydroxy-1-methylethyl)-2-propyl-1-((2'-(1H-tetrazol-5-yl)(1,1'-biphenyl)-4-yl)methyl-1H-Imidazole-5-carboxylic acid, (5-methyl -2-oxo-1,3-dioxol-4-yl;Olmesartan(144689-63-4);1H-Imidazole-5-carboxylic acid;

Article Data 49

Olmesartan medoxomil Synthetic route

144690-92-6

trityl olmesartan medoxomil

144689-63-4

olmesartan medoxomil

Conditions
ConditionsYield
With acetic acid In water at 25℃; for 1h;100%
With hydrogenchloride In water; toluene at 20℃; for 2.5h;98.6%
With TRILITE SCR-10 gel type In methanol for 6h; Product distribution / selectivity; Reflux;94%

(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 1-({2'-[1-(2,4-dimethoxybenzyl)-1H-tetrazol-5-yl]biphenyl-4-yl}methyl)-4-(1-hydroxy-1-methylethyl)-2-propyl-1H-imidazole-5-carboxylate

144689-63-4

olmesartan medoxomil

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane at 25℃; for 6h; Time;98%
144690-92-6

trityl olmesartan medoxomil

A

76-84-6

triphenylmethyl alcohol

B

144689-63-4

olmesartan medoxomil

Conditions
ConditionsYield
Stage #1: trityl olmesartan medoxomil With sulfuric acid; water In acetone at 40℃; for 2 - 4h;
Stage #2: With sodium hydrogencarbonate at 20℃; for 1h;		A n/a
B 90%
With water In acetone for 14h; Product distribution / selectivity; Heating / reflux;A n/a
B 73%
With water In acetonitrile for 14h; Product distribution / selectivity; Heating / reflux;A n/a
B 71%
80841-78-7

4-chloromethyl-5-methyl-1,3-dioxol-2-one

172875-59-1

ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-1-[2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl]methyl-1H-imidazole-5-carboxylate

144689-63-4

olmesartan medoxomil

Conditions
ConditionsYield
Stage #1: ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-1-[2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl]methyl-1H-imidazole-5-carboxylate With sodium hydroxide In N,N-dimethyl acetamide at 10 - 15℃; for 8h;
Stage #2: 4-chloromethyl-5-methyl-1,3-dioxol-2-one With potassium carbonate In N,N-dimethyl acetamide at 0 - 65℃; for 10h;		90%

trityl olmesartan medoxomil

144689-63-4

olmesartan medoxomil

Conditions
ConditionsYield
With hydrogenchloride In water; toluene at 20℃; for 3h;89%

(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-(1-hydroxy-1-methylethyl)-1-({2'-[1-(4-methoxybenzyl)-1H-tetrazol-5-yl]biphenyl-4-yl}methyl)-2-propyl-1H-imidazole-5-carboxylate

144689-63-4

olmesartan medoxomil

Conditions
ConditionsYield
With trifluoroacetic acid at 25℃; for 72h; Temperature;83%
1020157-01-0

(5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl4-(1-hydroxy-1-methylethyl)-2-propyl-1-[2′-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl]methyl-1H-imidazole-5-carboxylate

144689-63-4

olmesartan medoxomil

Conditions
ConditionsYield
With acetic acid at 80℃; for 2.5h;81%
With sulfuric acid In water; acetone at 50 - 55℃; for 2h;80%
With acetic acid In water at 55 - 60℃; for 2 - 3h; Product distribution / selectivity;
With hydrogenchloride In methanol; dichloromethane at 0 - 5℃; for 1 - 2h;
144690-33-5

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-({2'-[1-(triphenylmethyl)-1H-1,2,3,4-tetrazol-5-yl]-[1,1'-biphenyl]-4-yl}methyl)-1H-imidazole-5-carboxylate

144689-63-4

olmesartan medoxomil

Conditions
ConditionsYield
71%
Multi-step reaction with 2 steps
1.1: diisopropylamine; sodium hydroxide / toluene; ISOPROPYLAMIDE / 4 h / 25 - 45 °C
1.2: 8 h / 40 - 70 °C
1.3: 25 - 35 °C / pH ~ 6 - 7
2.1: hydrogenchloride; water / methanol / 1 h / 0 - 35 °C
2.2: 25 - 35 °C / pH ~ 3 - 4
View Scheme
Multi-step reaction with 3 steps
1.1: potassium carbonate; water / acetone / 16 h / 20 °C
2.1: potassium carbonate; potassium iodide / acetone / 3 h / 50 - 55 °C
3.1: hydrogenchloride; water / toluene / 3 h / 20 °C
3.2: 15 - 20 °C / pH 4.5 - 5.5
View Scheme
58954-23-7

2-propyl-1H-imidazole-4,5-dicarboxylic acid

144689-63-4

olmesartan medoxomil

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 86 percent / HCl / Ambient temperature
2: 95 percent / diethyl ether; CH2Cl2 / 1 h / 10 - 15 °C
3: 1.) t-BuOK / 1.) DMA, 0 deg C, 10 min, 2.) DMA, RT, 1 h
4: LiOH*H2O / dioxane; H2O / 20 h / Ambient temperature
5: 88 percent / K2CO3 / N,N-dimethyl-acetamide / 4 h / 20 - 50 °C
6: 81 percent / 25percent aq. AcOH / 2.5 h / 80 °C
View Scheme
133051-88-4

N-(triphenylmethyl)-5-<4'-(bromomethyl)biphenyl-2-yl>tetrazole

144689-63-4

olmesartan medoxomil

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 1.) t-BuOK / 1.) DMA, 0 deg C, 10 min, 2.) DMA, RT, 1 h
2: LiOH*H2O / dioxane; H2O / 20 h / Ambient temperature
3: 88 percent / K2CO3 / N,N-dimethyl-acetamide / 4 h / 20 - 50 °C
4: 81 percent / 25percent aq. AcOH / 2.5 h / 80 °C
View Scheme
Multi-step reaction with 4 steps
1: potassium iodide; potassium carbonate / N,N-dimethyl-formamide / 24 h / 20 °C
2: potassium hydroxide; water / N,N-dimethyl-formamide / 22 h / 54 - 56 °C
3: potassium iodide; potassium carbonate / 20 °C
4: sulfuric acid / water; acetone / 2 h / 50 - 55 °C
View Scheme

Olmesartan medoxomil Chemical Properties

Molecular Structure of Olmesartan medoxomil (CAS NO.144689-63-4):

IUPAC Name: (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 5-(2-hydroxypropan-2-yl)-2-propyl-3-[[4-[2-(2H-tetrazol-5-yl)phenyl]phenyl]methyl]imidazole-4-carboxylate
Molecular formula: C29H30N6O6
Molecular Weight: 558.5851
H bond acceptors: 12
H bond donors: 2
Freely Rotating Bonds: 12
Polar Surface Area: 132.48Å2
Index of Refraction: 1.661
Molar Refractivity: 149.19 cm3
Molar Volume: 403.5 cm3
Surface Tension: 53.6 dyne/cm
Density: 1.38 g/cm3
Flash Point: 440.2 °C
Enthalpy of Vaporization: 122.61 kJ/mol
Boiling Point: 804.2 °C at 760 mmHg
Vapour Pressure: 2.63E-27 mmHg at 25°C
Melting point: 180°C
Decomposition: 180 oC
Appearance: White to off-white crystalline powder
InChI
InChI=1/C29H30N6O6/c1-5-8-23-30-25(29(3,4)38)24(27(36)39-16-22-17(2)40-28(37)41-22)35(23)15-18-11-13-19(14-12-18)20-9-6-7-10-21(20)26-31-33-34-32-26/h6-7,9-14,38H,5,8,15-16H2,1-4H3,(H,31,32,33,34)
Smiles
c1(n(Cc2ccc(cc2)c2ccccc2c2nnn[nH]2)c(C(=O)OCc2oc(oc2C)=O)c(n1)C(C)(O)C)CCC
Product Categories: Active Pharmaceutical Ingredients; Aromatics; Bases & Related Reagents; Heterocycles; Intermediates & Fine Chemicals; Nucleotides; Pharmaceuticals; Olmesartan

Olmesartan medoxomil Specification

  Olmesartan medoxomil , with CAS number of 144689-63-4, can be called 4-(1-Hydroxy-1-methylethyl)-2-propyl-1-[[2(1H-tetazol-5-yl)[1,1biphenyl]-4-yl]methyl]-1H-imidazole-5-carboxylic Acid (5-Methyl-2-oxo-1,3-dioxol-4-yl)methyl Ester ; Oimesartan ; 4-(1-hydroxy-1-methylethyl)-2-propyl-1-((2'-(1H-tetrazol-5-yl)(1,1'-biphenyl)-4-yl)methyl-1H-Imidazole-5-carboxylic acid, (5-methyl -2-oxo-1,3-dioxol-4-yl) methyl ester ; Benicar . Olmesartan medoxomil is an angiotensin II receptor antagonist. It is used as an anti-hypertensive.

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