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Aliskiren

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Name

Aliskiren

EINECS 605-672-4
CAS No. 173334-57-1 Density 1.067 g/cm3
PSA 146.13000 LogP 5.08500
Solubility N/A Melting Point 98-99 °C
Formula C30H53 N3 O6 Boiling Point 748.4 °C at 760 mmHg
Molecular Weight 551.767 Flash Point 406.4 °C
Transport Information N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 173334-57-1 (Aliskiren) Hazard Symbols N/A
Synonyms

Benzeneoctanamide,d-amino-N-(3-amino-2,2-dimethyl-3-oxopropyl)-g-hydroxy-4-methoxy-3-(3-methoxypropoxy)-a,z-bis(1-methylethyl)-,(aS,gS,dS,zS)-;(2S,4S,5S,7S)-5-Amino-N-(3-amino-2,2-dimethyl-3-oxopropyl)-4-hydroxy-2-isopropyl-7-[4-methoxy-3-(3-methoxypropoxy)benzyl]-8-methylnonanamide;Rasilez;Tekturna;

Article Data 32

Aliskiren Synthetic route

173338-07-3

tert-butyl (3S,5S,6S,8S)-8-(3-amino-2,2-dimethyl-3-oxopropylcarbamoyl)-6-hydroxy-3-(4-methoxy-3-(3-methoxypropoxy)benzyl)-2,9-dimethyldecan-5-ylcarbamate

173334-57-1

(2S,4S,5S,7S)-5-Amino-4-hydroxy-2-isopropyl-7-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-8-methyl-nonanoic acid (2-carbamoyl-2-methyl-propyl)-amide

Conditions
ConditionsYield
Stage #1: tert-butyl (3S,5S,6S,8S)-8-(3-amino-2,2-dimethyl-3-oxopropylcarbamoyl)-6-hydroxy-3-(4-methoxy-3-(3-methoxypropoxy)benzyl)-2,9-dimethyldecan-5-ylcarbamate With hydrogenchloride In dichloromethane at 0 - 5℃;
Stage #2: With sodium hydroxide In dichloromethane pH=9;
100%
With hydrogenchloride In 1,4-dioxane at 0℃; Inert atmosphere;99%
With hydrogenchloride; water In ethyl acetate at 20℃; for 0.0833333h; Flow reactor;96%
1236549-06-6

(1S,2S,4S)-4-(2-carbamoyl-2-methylpropyl-carbamoyl)-2-hydroxy-1-{(S)-2-[4-methoxy-3-(3-methoxypropoxy)-benzyl]-3-methylbutyl}-5-methylhexyl-carbamic acid benzyl ester

173334-57-1

(2S,4S,5S,7S)-5-Amino-4-hydroxy-2-isopropyl-7-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-8-methyl-nonanoic acid (2-carbamoyl-2-methyl-propyl)-amide

Conditions
ConditionsYield
With 10% palladium on activated charcoal; hydrogen97%
With 5%-palladium/activated carbon; hydrogen In tert-butyl methyl ether at 25℃; under 2280.15 Torr; for 16h;86%
With 5%-palladium/activated carbon; hydrogen In tert-butyl methyl ether at 25℃; under 2280.15 Torr; for 16h;86%
Stage #1: (1S,2S,4S)-4-(2-carbamoyl-2-methylpropyl-carbamoyl)-2-hydroxy-1-{(S)-2-[4-methoxy-3-(3-methoxypropoxy)-benzyl]-3-methylbutyl}-5-methylhexyl-carbamic acid benzyl ester With hydrogen; acetic acid; palladium 10% on activated carbon In ethanol at 20℃; under 760.051 Torr;
Stage #2: With sodium hydroxide In ethanol pH=10;
Stage #1: (1S,2S,4S)-4-(2-carbamoyl-2-methylpropyl-carbamoyl)-2-hydroxy-1-{(S)-2-[4-methoxy-3-(3-methoxypropoxy)-benzyl]-3-methylbutyl}-5-methylhexyl-carbamic acid benzyl ester With hydrogen; acetic acid; palladium 10% on activated carbon In ethanol at 20℃; under 760.051 Torr;
Stage #2: With sodium hydroxide In ethanol; water pH=10;

C37H59N3O6

173334-57-1

(2S,4S,5S,7S)-5-Amino-4-hydroxy-2-isopropyl-7-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-8-methyl-nonanoic acid (2-carbamoyl-2-methyl-propyl)-amide

Conditions
ConditionsYield
With hydrogen; ethanolamine; 10% palladium on activated carbon In methanol at 20℃; under 760.051 Torr; for 3h;87%
324763-51-1

aminopivalinamide

C29H49NO6S

173334-57-1

(2S,4S,5S,7S)-5-Amino-4-hydroxy-2-isopropyl-7-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-8-methyl-nonanoic acid (2-carbamoyl-2-methyl-propyl)-amide

Conditions
ConditionsYield
With 2-hydroxypyridin; hydrogenchloride; triethylamine In methanol at 80℃;68%

3-amino-2,2-dimethylpropionamide ammonium chloride

1,1-dimethylethyl[(1S,3S)-3-[{4-methoxy-3-(3-methoxypropoxy)phenyl}methyl]-4-methyl-1-[tetrahydro-4-(1-methylethyl)-5-oxo-2-furanyl]pentyl]carbamate

173334-57-1

(2S,4S,5S,7S)-5-Amino-4-hydroxy-2-isopropyl-7-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-8-methyl-nonanoic acid (2-carbamoyl-2-methyl-propyl)-amide

Conditions
ConditionsYield
Stage #1: 3-amino-2,2-dimethylpropionamide ammonium chloride; 1,1-dimethylethyl[(1S,3S)-3-[{4-methoxy-3-(3-methoxypropoxy)phenyl}methyl]-4-methyl-1-[tetrahydro-4-(1-methylethyl)-5-oxo-2-furanyl]pentyl]carbamate; sodium 2-ethylhexanoic acid at 120℃; for 1h;
Stage #2: With amine HCl
Stage #3: With NaA Product distribution / selectivity;
40%

(2S,4S,5S,7S)-N-(3-amino-2,2-dimethyl-3-oxopropyl)-5-azido-4-hydroxy-2-isopropyl-7-[4-methoxy-3-(3-methoxypropoxy)benzyl]-8-methylnonanamide

173334-57-1

(2S,4S,5S,7S)-5-Amino-4-hydroxy-2-isopropyl-7-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-8-methyl-nonanoic acid (2-carbamoyl-2-methyl-propyl)-amide

Conditions
ConditionsYield
With palladium on activated charcoal; hydrogen In methanol at 20℃; for 3h;38%
324763-47-5

(2S,4S,5S,7S)-N-(3-amino-2,2-dimethyl-3-oxopropyl)-5-azido-4-hydroxy-2-isopropyl-7-(4-methoxy-3-(methoxypropoxy)benzyl)-8-methylnonanamide

173334-57-1

(2S,4S,5S,7S)-5-Amino-4-hydroxy-2-isopropyl-7-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-8-methyl-nonanoic acid (2-carbamoyl-2-methyl-propyl)-amide

Conditions
ConditionsYield
With hydrogenchloride; hydrogen; palladium on activated charcoal In methanol
With 1% Pd/C; hydrogen In ethanol
In methanol
With hydrogen; ethanolamine; palladium 10% on activated carbon In isopropyl alcohol for 3h; Product distribution / selectivity;
With palladium 10% on activated carbon; ammonia; hydrogen In ethanol at 20℃; under 5250.53 Torr;
666844-61-7

(2-carbamoyl-2-methylpropyl)carbamic acid benzyl ester

173334-57-1

(2S,4S,5S,7S)-5-Amino-4-hydroxy-2-isopropyl-7-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-8-methyl-nonanoic acid (2-carbamoyl-2-methyl-propyl)-amide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: H2 / Pd()OH)2/C
2: 65 percent / 2-hydroxypyridine; Et3N
3: TMSCl; phenol / CH2Cl2
View Scheme
172900-83-3

(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester

173334-57-1

(2S,4S,5S,7S)-5-Amino-4-hydroxy-2-isopropyl-7-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-8-methyl-nonanoic acid (2-carbamoyl-2-methyl-propyl)-amide

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: Mg
2: 23 percent / H2 / Pd(OH)2/C
3: 38 percent / TPAP; NMMO
4: 65 percent / 2-hydroxypyridine; Et3N
5: TMSCl; phenol / CH2Cl2
View Scheme
866030-33-3

(2R,5S)-3,6-diethoxy-2-isopropyl-5-((S)-2-(4-methoxy-3-(3-methoxypropoxy)benzyl)-3-methylbutyl)-2,5-dihydropyrazine

173334-57-1

(2S,4S,5S,7S)-5-Amino-4-hydroxy-2-isopropyl-7-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-8-methyl-nonanoic acid (2-carbamoyl-2-methyl-propyl)-amide

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: HCl / acetonitrile
2: Et3N
3: NaBH4 / ethanol
4: 89 percent / DMSO; ClC(O)C(O)Cl; Et3N / CH2Cl2
5: Mg
6: 23 percent / H2 / Pd(OH)2/C
7: 38 percent / TPAP; NMMO
8: 65 percent / 2-hydroxypyridine; Et3N
9: TMSCl; phenol / CH2Cl2
View Scheme

Aliskiren Chemical Properties

Structure of Aliskiren (CAS NO.173334-57-1):
                          
IUPAC Name: (2S,4S,5S,7S)-5-amino-N-(3-amino-2,2-dimethyl-3-oxopropyl)-4-hydroxy-7-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-8-methyl-2-propan-2-ylnonanamideMolecular
Empirical Formula of Aliskiren (CAS NO.173334-57-1): C30H53N3O6
Molecular Weight: 551.7583 g/mol
H bond acceptors: 9
H bond donors: 6
Freely Rotating Bonds: 21
Index of Refraction: 1.513
Molar Refractivity: 155.53 cm3
Molar Volume: 516.9 cm3
Surface Tension: 40.5 dyne/cm
Index of Refraction: 1.513
Density: 1.067 g/cm3
Flash Point: 406.4 °C
Enthalpy of Vaporization: 114.48 kJ/mol
Boiling Point: 748.4 °C at 760 mmHg
Vapour Pressure: 1.59E-23 mmHg at 25 °C
Product Categories: Chemical Amines; Amines; Chiral Reagents; Intermediates & Fine Chemicals; Pharmaceuticals
InChI
InChI=1/C30H53N3O6/c1-19(2)22(14-21-10-11-26(38-8)27(15-21)39-13-9-12-37-7)16-24(31)25(34)17-23(20(3)4)28(35)33-18-30(5,6)29(32)36/h10-11,15,19-20,22-25,34H,9,12-14,16-18,31H2,1-8H3,(H2,32,36)(H,33,35)/t22-,23+,24-,25-/m0/s1
Smiles
C([C@@H](C[C@H](N)[C@H](C[C@@H](C(NCC(C(N)=O)(C)C)=O)C(C)C)O)C(C)C)c1ccc(OC)c(OCCCOC)c1

Aliskiren Specification

  Aliskiren , its cas register number is 173334-57-1. It also can be called (2S,4S,5S,7S)-5-Amino-N-(2-carbamoyl-2-methylpropyl)-4-hydroxy-2-isopropyl-7-[4-methoxy-3-(3-methoxypropoxy)benzyl]-8-methylnonanamide and Tekturna . It is an orally active, synthetic nonpeptide renin inhibitor, used to be antihypertensive.

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