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173334-58-2

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Basic Information
CAS No.: 173334-58-2
Name: Aliskiren hemifumarate
Article Data: 15
Molecular Structure:
Molecular Structure of 173334-58-2 (Aliskiren hemifumarate)
Formula: 2(C30H53N3O6).C4H4O4
Molecular Weight: 609.804
Synonyms: Aliskiren fumarate;Bis(2S,4S,5S,7S)-5-amino-N-(3-amino-2,2-dimethyl-3-oxopropyl)-4-hydroxy-7-(4-methoxy-3-(3-methoxypropoxy)benzyl)-8-methyl-2-(1-methylethyl)nonanamide) (2E)-but-2-enedioate;
EINECS: 630-415-8
Melting Point: 72-75?C
Boiling Point: 748.4 °C at 760 mmHg
Flash Point: 406.4 °C
Appearance: white powder
PSA: 366.86000
LogP: 9.88180
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Synthetic route
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

110-17-8

(2E)-but-2-enedioic acid

173334-58-2

(2S,4S,5S,7S)-5-amino-N-(3-amino-2,2-dimethyl-3-oxypropyl)-4-hydroxy-7-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-8-methyl-(2-propan-2-yl)nonanamide hemifumarate

Conditions
ConditionsYield
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 palladium 10% on activated carbon; hydrogen In isopropyl alcohol at 20℃; under 760.051 Torr;
Stage #2: (2E)-but-2-enedioic acid In ethanol		100%
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 palladium 10% on activated carbon In isopropyl alcohol at 20℃; under 760.051 Torr;
Stage #2: (2E)-but-2-enedioic acid In ethanol		85%
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

110-17-8

(2E)-but-2-enedioic acid

173334-58-2

(2S,4S,5S,7S)-5-amino-N-(3-amino-2,2-dimethyl-3-oxypropyl)-4-hydroxy-7-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-8-methyl-(2-propan-2-yl)nonanamide hemifumarate

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℃; for 3h;
Stage #2: (2E)-but-2-enedioic acid In ethanol		85%
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℃; for 3h;
Stage #2: (2E)-but-2-enedioic acid In ethanol		85%
110-17-8

(2E)-but-2-enedioic acid

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

173334-58-2

(2S,4S,5S,7S)-5-amino-N-(3-amino-2,2-dimethyl-3-oxypropyl)-4-hydroxy-7-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-8-methyl-(2-propan-2-yl)nonanamide hemifumarate

Conditions
ConditionsYield
In methanol Solvent; Concentration; Time; Temperature;81.5%
In methanol at 35℃; for 1h; Product distribution / selectivity;74.25%
In ethanol at 20℃; Product distribution / selectivity;
173399-03-6

aliskiren

110-17-8

(2E)-but-2-enedioic acid

173334-58-2

(2S,4S,5S,7S)-5-amino-N-(3-amino-2,2-dimethyl-3-oxypropyl)-4-hydroxy-7-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-8-methyl-(2-propan-2-yl)nonanamide hemifumarate

Conditions
ConditionsYield
Stage #1: aliskiren With sodium hydroxide In water at 0℃;
Stage #2: (2E)-but-2-enedioic acid In methanol

(2S,4S,5S,7S)-N-(2-carbamoyl-2-methylpropyl)-5-amino-4-hydroxy-2,7-diisopropyl-8-[4-methoxy-3-(3-methoxypropoxy)phenyl]octanamide

110-17-8

(2E)-but-2-enedioic acid

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

A

173334-58-2

(2S,4S,5S,7S)-5-amino-N-(3-amino-2,2-dimethyl-3-oxypropyl)-4-hydroxy-7-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-8-methyl-(2-propan-2-yl)nonanamide hemifumarate

B

0.5C4H4O4*C30H53N3O6

Conditions
ConditionsYield
In ethanol at 40℃; Product distribution / selectivity;A 93 %Chromat.
B n/a
...Expand

0.5C4H4O4*C30H53N3O6

173334-58-2

(2S,4S,5S,7S)-5-amino-N-(3-amino-2,2-dimethyl-3-oxypropyl)-4-hydroxy-7-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-8-methyl-(2-propan-2-yl)nonanamide hemifumarate

Conditions
ConditionsYield
In ethanol; acetonitrile at 20℃; Purification / work up;98.8 %Chromat.
324763-51-1

aminopivalinamide

173334-58-2

(2S,4S,5S,7S)-5-amino-N-(3-amino-2,2-dimethyl-3-oxypropyl)-4-hydroxy-7-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-8-methyl-(2-propan-2-yl)nonanamide hemifumarate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: triethylamine; 2-hydroxypyridin / 16 h / 85 - 90 °C
2: hydrogen; ethanolamine / palladium 10% on activated carbon / isopropyl alcohol / 3 h
3: ethanol / 0.17 h / 25 - 30 °C
View Scheme
Multi-step reaction with 2 steps
1.1: 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / 4 h / 75 - 80 °C
1.2: 15 h / 85 - 90 °C
1.3: 3 h
2.1: ethanol / 0.17 h / 25 - 30 °C
View Scheme
Multi-step reaction with 4 steps
1.1: thionyl chloride / 1,2-dichloro-ethane / 5 h / 75 - 80 °C
1.2: 90 - 95 °C
1.3: 10 - 15 °C / pH 14
2.1: triethylamine; 2-hydroxypyridin / 30 h / 80 - 90 °C
3.1: sodium hydroxide; dihydrogen peroxide / water / 20 - 40 °C
4.1: hydrogen; ethanolamine / 5%-palladium/activated carbon / ethanol / 2206.72 Torr
View Scheme
503-74-2

3-methylbutyric acid

173334-58-2

(2S,4S,5S,7S)-5-amino-N-(3-amino-2,2-dimethyl-3-oxypropyl)-4-hydroxy-7-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-8-methyl-(2-propan-2-yl)nonanamide hemifumarate

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1.1: dmap / 1,1-dichloroethane / 0.5 h / 20 °C
1.2: 14.5 h / 10 - 30 °C
2.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -70 °C / Inert atmosphere
2.2: -70 - 5 °C
3.1: dihydrogen peroxide; lithium hydroxide monohydrate / water; tetrahydrofuran / 0 - 30 °C
4.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere
4.2: 5.75 h / 0 - 30 °C
5.1: N-chloro-succinimide; triphenylphosphine / dichloromethane / 5.5 h / -40 - 30 °C
6.1: magnesium; ethylene dibromide / tetrahydrofuran / 4.17 h / 63 - 68 °C / Inert atmosphere
6.2: 12.5 h / 0 - 5 °C
7.1: water; lithium hydroxide / tetrahydrofuran; methanol / 26 h / 65 - 70 °C
7.2: 0.5 h / 0 - 5 °C
8.1: hydrogenchloride / 1,1-dichloroethane; water / 0 - 5 °C / pH 2.5
8.2: 14.25 h / 0 - 30 °C
9.1: N-Bromosuccinimide; phosphoric acid / water; tetrahydrofuran / 1.25 h / 0 - 5 °C
10.1: sodium azide / ethylene glycol / 20 h / 80 - 85 °C
11.1: triethylamine; 2-hydroxypyridin / 16 h / 85 - 90 °C
12.1: hydrogen; ethanolamine / palladium 10% on activated carbon / isopropyl alcohol / 3 h
13.1: ethanol / 0.17 h / 25 - 30 °C
View Scheme
Multi-step reaction with 10 steps
1.1: dmap / 1,1-dichloroethane / 0.5 h / 20 °C
1.2: 14.5 h / 10 - 30 °C
2.1: titanium(IV) isopropylate; N-ethyl-N,N-diisopropylamine; titanium tetrachloride / dichloromethane / 1 h / 0 - 5 °C / Inert atmosphere
2.2: -30 - -25 °C
2.3: -30 - 5 °C
3.1: hydrogen; acetic acid / palladium on activated charcoal / 60 - 70 °C / 2942.29 Torr
4.1: dihydrogen peroxide; lithium hydroxide monohydrate / water; tetrahydrofuran / 0 - 30 °C
5.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere
5.2: 5.75 h / 0 - 30 °C
6.1: N-chloro-succinimide; triphenylphosphine / dichloromethane / 5.5 h / -40 - 30 °C
7.1: magnesium; ethylene dibromide / tetrahydrofuran / 4.17 h / 63 - 68 °C / Inert atmosphere
7.2: 1 h / 0 - 5 °C
8.1: N-Bromosuccinimide; phosphoric acid / water; tetrahydrofuran / 1.25 h / 0 - 5 °C
9.1: 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / 4 h / 75 - 80 °C
9.2: 15 h / 85 - 90 °C
9.3: 3 h
10.1: ethanol / 0.17 h / 25 - 30 °C
View Scheme
Multi-step reaction with 10 steps
1.1: dmap / 1,1-dichloroethane / 0.5 h / 20 °C
1.2: 14.5 h / 10 - 30 °C
2.1: titanium(IV) isopropylate; N-ethyl-N,N-diisopropylamine; titanium tetrachloride / dichloromethane / 1 h / 0 - 5 °C / Inert atmosphere
2.2: -30 - -25 °C
2.3: -30 - 5 °C
3.1: hydrogen; acetic acid / palladium on activated charcoal / 60 - 70 °C / 2942.29 Torr
4.1: sodium tetrahydroborate / tetrahydrofuran / 0 - 15 °C
4.2: 11 h / 60 - 65 °C
5.1: N-chloro-succinimide; triphenylphosphine / dichloromethane / 5.5 h / -40 - 30 °C
6.1: magnesium; ethylene dibromide / tetrahydrofuran / 4.17 h / 63 - 68 °C / Inert atmosphere
6.2: 1 h / 0 - 5 °C
6.3: 0.75 h / 0 - 5 °C
7.1: sodium azide / ethylene glycol / 20 h / 80 - 85 °C
8.1: triethylamine; 2-hydroxypyridin / 16 h / 85 - 90 °C
9.1: hydrogen; ethanolamine / palladium 10% on activated carbon / isopropyl alcohol / 3 h
10.1: ethanol / 0.17 h / 25 - 30 °C
View Scheme
7505-93-3

2-cyano-2-methylpropanamide

173334-58-2

(2S,4S,5S,7S)-5-amino-N-(3-amino-2,2-dimethyl-3-oxypropyl)-4-hydroxy-7-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-8-methyl-(2-propan-2-yl)nonanamide hemifumarate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: hydrogen; ammonia / raney nickel / methanol / 14 h / 40 - 45 °C / 2942.29 Torr
2: triethylamine; 2-hydroxypyridin / 16 h / 85 - 90 °C
3: hydrogen; ethanolamine / palladium 10% on activated carbon / isopropyl alcohol / 3 h
4: ethanol / 0.17 h / 25 - 30 °C
View Scheme
Multi-step reaction with 3 steps
1.1: hydrogen; ammonia / raney nickel / methanol / 14 h / 40 - 45 °C / 2942.29 Torr
2.1: 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / 4 h / 75 - 80 °C
2.2: 15 h / 85 - 90 °C
2.3: 3 h
3.1: ethanol / 0.17 h / 25 - 30 °C
View Scheme
110-17-8

(2E)-but-2-enedioic acid

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

173334-58-2

(2S,4S,5S,7S)-5-amino-N-(3-amino-2,2-dimethyl-3-oxypropyl)-4-hydroxy-7-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-8-methyl-(2-propan-2-yl)nonanamide hemifumarate

Conditions
ConditionsYield
Stage #1: (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 With hydrogen; ethanolamine; 5%-palladium/activated carbon In ethanol under 2206.72 Torr;
Stage #2: (2E)-but-2-enedioic acid In ethanol Product distribution / selectivity;
Raw Materials
173334-57-1
110-17-8
67744-70-1
503-74-2
324763-51-1
173399-03-6
173338-07-3
324763-47-5
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173334-57-1
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Chemistry

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-ylnonanamide; (E)-but-2-enedioic acid
Synonyms of Aliskiren hemifumarate (CAS NO.173334-58-2): Aliskiren fumarate ; Bis(2S,4S,5S,7S)-5-amino-N-(3-amino-2,2-dimethyl-3-oxopropyl)-4-hydroxy-7-(4-methoxy-3-(3-methoxypropoxy)benzyl)-8-methyl-2-(1-methylethyl)nonanamide) (2E)-but-2-enedioate ; Tekturna
CAS NO: 173334-58-2
Molecular Formula: 2(C30H53N3O6).C4H4O4
Molecular Weight: 1219.60
Molecular Structure: