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151767-02-1

Basic Information
CAS No.: 151767-02-1
Name: Montelukast sodium
Article Data: 81
Cas Database
Molecular Structure:
Molecular Structure of 151767-02-1 (Montelukast sodium)
Formula: C35H35ClNNaO3S
Molecular Weight: 608.177
Synonyms: Cyclopropaneacetic acid,1-[[[(1R)-1-[3-[(1E)-2-(7-chloro-2- quinolinyl)ethenyl]phenyl]-3-[2-(1-hydroxy- 1-methylethyl)phenyl]propyl]thio]methyl]-,monosodium salt;Singulair (TN);Singulair;sodium 2-[1-[[(1R)-1-[3-[2-(7-chloroquinolin-2-yl)ethenyl]phenyl]-3-[2-(2-hydroxypropan-2-yl)phenyl]propyl]sulfanylmethyl]cyclopropyl]acetate;MK 476;
EINECS: 604-813-7
Density: N/A
Melting Point: 115 °C(dec.)
Boiling Point: 750.5 °C at 760 mmHg
Flash Point: 407.7 °C
Solubility: N/A
Appearance: White to off-white crystalline powder
Hazard Symbols: Xi
Risk Codes: 63-41-62
Safety: 26
Transport Information: N/A
PSA: N/A
LogP: N/A
Synthetic route
1310-73-2

sodium hydroxide

158966-92-8

montelukast

151767-02-1

Montelukast sodium

Conditions
ConditionsYield
In methanol; toluene at 20℃; for 1h; Product distribution / selectivity;100%
In methanol; toluene at 2 - 20℃; for 0.75h; Product distribution / selectivity;100%
In methanol at 20℃; for 1h; Product distribution / selectivity;73%
In methanol at 25 - 35℃; for 0.166667h;
158966-92-8

montelukast

151767-02-1

Montelukast sodium

Conditions
ConditionsYield
With sodium hydroxide In methanol; toluene at 20℃; for 1h;100%
With sodium hydroxide In methanol; water; toluene for 0.5h; Product distribution / selectivity; Alkaline aqueous solution;98%
With sodium hydroxide In methanol at -5 - 35℃; for 1h;98.7%
577953-88-9

1-(((1(R)-(3-(2-(7-chloro-2-quinolinil)ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropane acetic acid dicyclohexylamine salt

151767-02-1

Montelukast sodium

Conditions
ConditionsYield
Stage #1: 1-(((1(R)-(3-(2-(7-chloro-2-quinolinil)ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropane acetic acid dicyclohexylamine salt With acetic acid In dichloromethane pH=4 - 4.5;
Stage #2: With pyrographite; sodium hydroxide In methanol; water for 1h;
99%
Stage #1: 1-(((1(R)-(3-(2-(7-chloro-2-quinolinil)ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropane acetic acid dicyclohexylamine salt With acetic acid In dichloromethane; water pH=4 - 4.5;
Stage #2: With pyrographite; sodium hydroxide In methanol; water for 1h;
99%
Stage #1: 1-(((1(R)-(3-(2-(7-chloro-2-quinolinil)ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropane acetic acid dicyclohexylamine salt With acetic acid In water; toluene at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: With sodium hydroxide In methanol at 20 - 25℃; for 2h; Inert atmosphere;
94%
880769-29-9

1-(((1(R)-(3-(2-(7-chloro-2-quinolinil)ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropane acetic acid α-methylbenzylamine salt

151767-02-1

Montelukast sodium

Conditions
ConditionsYield
Stage #1: 1-(((1(R)-(3-(2-(7-chloro-2-quinolinil)ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropane acetic acid α-methylbenzylamine salt With acetic acid In dichloromethane pH=4 - 4.5;
Stage #2: With pyrographite; sodium hydroxide In methanol; water for 1h;
99%
Stage #1: 1-(((1(R)-(3-(2-(7-chloro-2-quinolinil)ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropane acetic acid α-methylbenzylamine salt With acetic acid In dichloromethane; water pH=4 - 4.5;
Stage #2: With pyrographite; sodium hydroxide In methanol; water for 1h;
99%
Stage #1: 1-(((1(R)-(3-(2-(7-chloro-2-quinolinil)ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropane acetic acid α-methylbenzylamine salt With acetic acid In dichloromethane; water at 25 - 35℃; for 0.75h;
Stage #2: With sodium hydroxide In ethanol; dichloromethane at 25 - 30℃; for 1h; Product distribution / selectivity;
75.6%
Stage #1: 1-(((1(R)-(3-(2-(7-chloro-2-quinolinil)ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropane acetic acid α-methylbenzylamine salt With acetic acid In dichloromethane; water at 25 - 35℃;
Stage #2: With sodium hydroxide In ethanol at 25 - 30℃; Product distribution / selectivity;
75.6%
1100021-03-1

1-(((1(R)-(3-(2-(7-chloro-2-quinolinil)ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropane acetic acid benzylamine salt

151767-02-1

Montelukast sodium

Conditions
ConditionsYield
Stage #1: 1-(((1(R)-(3-(2-(7-chloro-2-quinolinil)ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropane acetic acid benzylamine salt With acetic acid In dichloromethane; water pH=4 - 4.5;
Stage #2: With pyrographite; sodium hydroxide In methanol; water for 1h;
99%
Stage #1: 1-(((1(R)-(3-(2-(7-chloro-2-quinolinil)ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropane acetic acid benzylamine salt With acetic acid In dichloromethane pH=4 - 4.5;
Stage #2: With pyrographite; sodium hydroxide In methanol; water for 1h;
1254938-23-2

1-(((1(R)-(3-(2-(7-chloro-2-quinolinil)ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropane acetic acid 4-chloro benzylamine salt

151767-02-1

Montelukast sodium

Conditions
ConditionsYield
Stage #1: 1-(((1(R)-(3-(2-(7-chloro-2-quinolinil)ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropane acetic acid 4-chloro benzylamine salt With acetic acid In dichloromethane pH=4 - 4.5;
Stage #2: With pyrographite; sodium hydroxide In methanol; water for 1h;
99%
Stage #1: 1-(((1(R)-(3-(2-(7-chloro-2-quinolinil)ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropane acetic acid 4-chloro benzylamine salt With acetic acid In dichloromethane; water pH=4 - 4.5;
Stage #2: With pyrographite; sodium hydroxide In methanol; water for 1h;
99%

1-(((1(R)-(3-(2-(7-chloro-2-quinolinil)ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropane acetic acid 4-methoxy benzylamine salt

151767-02-1

Montelukast sodium

Conditions
ConditionsYield
Stage #1: 1-(((1(R)-(3-(2-(7-chloro-2-quinolinil)ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropane acetic acid 4-methoxy benzylamine salt With acetic acid In dichloromethane pH=4 - 4.5;
Stage #2: With pyrographite; sodium hydroxide In methanol; water for 1h;
99%
Stage #1: 1-(((1(R)-(3-(2-(7-chloro-2-quinolinil)ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropane acetic acid 4-methoxy benzylamine salt With acetic acid In dichloromethane; water pH=4 - 4.5;
Stage #2: With pyrographite; sodium hydroxide In methanol; water for 1h;
99%
1310-73-2

sodium hydroxide

577953-88-9

1-(((1(R)-(3-(2-(7-chloro-2-quinolinil)ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropane acetic acid dicyclohexylamine salt

151767-02-1

Montelukast sodium

Conditions
ConditionsYield
Stage #1: 1-(((1(R)-(3-(2-(7-chloro-2-quinolinil)ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropane acetic acid dicyclohexylamine salt With water; acetic acid In toluene at 20 - 25℃; for 0.166667h;
Stage #2: sodium hydroxide In ethanol; water; toluene at 20℃; for 0.333333h;
98%
1254938-26-5

1-(((1(R)-(3-(2-(7-chloro-2-quinolinil)ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropane acetic acid 4-bromo benzylamine salt

151767-02-1

Montelukast sodium

Conditions
ConditionsYield
Stage #1: 1-(((1(R)-(3-(2-(7-chloro-2-quinolinil)ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropane acetic acid 4-bromo benzylamine salt With acetic acid In dichloromethane pH=4 - 4.5;
Stage #2: With pyrographite; sodium hydroxide In methanol; water for 1h;
98%
Stage #1: 1-(((1(R)-(3-(2-(7-chloro-2-quinolinil)ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropane acetic acid 4-bromo benzylamine salt With acetic acid In dichloromethane; water pH=4.5;
Stage #2: With pyrographite; sodium hydroxide In methanol; water for 1h;
98%

1-(((1-(R)-(3-(2-(7-chloro-2-quinolinyl)-ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropylacetate 2-amino-1-butanol

151767-02-1

Montelukast sodium

Conditions
ConditionsYield
Stage #1: 1-(((1-(R)-(3-(2-(7-chloro-2-quinolinyl)-ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropylacetate 2-amino-1-butanol With acetic acid In dichloromethane; water for 0.25h;
Stage #2: With pyrographite; sodium sulfate; sodium hydroxide In methanol at 15 - 25℃; for 1h; Temperature;
97.2%
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158966-92-8
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Specification

Montelukast sodium, its cas register number is 151767-02-1. It also can be called Singulair; montelukast na; montelukast sodium; 2-[1-[[1-[3-[2-[(7-chloro-2-quinolyl)]vinyl]phenyl]-3-[2-(1-hydroxy-1-methyl-ethyl)phenyl]-propyl]sulfanylmethyl]cyclopropyl]acetic acid sodium salt; montelukast, sodium salt. Montelukast sodium is a hygroscopic, optically active, white to off-white powder. Montelukast sodium is freely soluble in ethanol, methanol, and water and practically insoluble in acetonitrile. The empirical formula is C35H35CINNaO3S, and its molecular weight is 608.18. Montelukast sodium is a selective leukotriene D4-receptor antagonist, can be used as an antiasthmatic treatment of asthma and to relieve symptoms of seasonal allergies.

Physical properties about Montelukast sodium are: (1)ACD/LogP: 7.799; (2)# of Rule of 5 Violations: 2; (3)ACD/LogD (pH 5.5): 6.99; (4)ACD/LogD (pH 7.4): 5.19; (5)ACD/BCF (pH 5.5): 76510.22; (6)ACD/BCF (pH 7.4): 1223.10; (7)ACD/KOC (pH 5.5): 63978.22; (8)ACD/KOC (pH 7.4): 1022.76; (9)#H bond acceptors: 4; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 13; (12)Flash Point: 407.7 °C; (13)Enthalpy of Vaporization: 114.78 kJ/mol; (14)Boiling Point: 750.5 °C at 760 mmHg; (15)Vapour Pressure: 1.17E-23 mmHg at 25°C

You can still convert the following datas into molecular structure:
(1)InChI=1S/C35H36ClNO3S.Na/c1-34(2,40)30-9-4-3-7-25(30)13-17-32(41-23-35(18-19-35)22-33(38)39)27-8-5-6-24(20-27)10-15-29-16-12-26-11-14-28(36)21-31(26)37-29;/h3-12,14-16,20-21,32,40H,13,17-19,22-23H2,1-2H3,(H,38,39);/q;+1/p-1/b15-10+;/t32-;/m1./s1;
(2)InChIKey=LBFBRXGCXUHRJY-HKHDRNBDSA-M;
(3)SmilesC1(CC1)(CS[C@@H](c1cc(\C=C\c2nc3c(ccc(c3)Cl)cc2)ccc1)CCc1c(cccc1)C(C)(C)O)CC(=O)[O-].[Na+]

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