Product Name

  • Name

    Aliskiren

  • EINECS 605-672-4
  • CAS No. 173334-57-1
  • Article Data32
  • CAS DataBase
  • Density 1.067 g/cm3
  • Solubility
  • 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
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 173334-57-1 (Aliskiren)
  • Hazard Symbols
  • 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;
  • PSA 146.13000
  • LogP 5.08500

Synthetic route

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
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

(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
173334-57-1

(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%
(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
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

(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
173334-57-1

(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

C37H59N3O6

(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
173334-57-1

(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%
aminopivalinamide
324763-51-1

aminopivalinamide

C29H49NO6S

C29H49NO6S

(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
173334-57-1

(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

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

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

(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
173334-57-1

(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

(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

(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
173334-57-1

(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%
(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
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

(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
173334-57-1

(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;
(2-carbamoyl-2-methylpropyl)carbamic acid benzyl ester
666844-61-7

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

(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
173334-57-1

(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
(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester
172900-83-3

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

(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
173334-57-1

(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
(2R,5S)-3,6-diethoxy-2-isopropyl-5-((S)-2-(4-methoxy-3-(3-methoxypropoxy)benzyl)-3-methylbutyl)-2,5-dihydropyrazine
866030-33-3

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

(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
173334-57-1

(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
tert-butyl {(1S,3S)-1-((2S,4S)-4-isopropyl-5-oxotetrahydrofuran-2-yl)-3-[4-methoxy-3-(3-methoxypropoxy)benzyl]-4-methylpentyl}carbamate
866030-35-5

tert-butyl {(1S,3S)-1-((2S,4S)-4-isopropyl-5-oxotetrahydrofuran-2-yl)-3-[4-methoxy-3-(3-methoxypropoxy)benzyl]-4-methylpentyl}carbamate

(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
173334-57-1

(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 2 steps
1: 65 percent / 2-hydroxypyridine; Et3N
2: TMSCl; phenol / CH2Cl2
View Scheme
Multi-step reaction with 2 steps
1.1: triethylamine; 2-hydroxypyridin / tert-butyl methyl ether / 18 h / 80 °C
2.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C
2.2: pH 10
View Scheme
Multi-step reaction with 2 steps
1.1: triethylamine; 2-hydroxypyridin / 36 h / 60 - 65 °C
2.1: hydrogenchloride / dichloromethane; water / 3 h / 0 - 5 °C
2.2: 0 - 5 °C
View Scheme
((1S,2S,4S)-2-hydroxy-4-hydroxymethyl-1-((S)-2-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-3-methyl-butyl)-5-methyl-hexyl)-carbamic acid tert-butyl ester
866030-34-4

((1S,2S,4S)-2-hydroxy-4-hydroxymethyl-1-((S)-2-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-3-methyl-butyl)-5-methyl-hexyl)-carbamic acid tert-butyl ester

(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
173334-57-1

(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: 38 percent / TPAP; NMMO
2: 65 percent / 2-hydroxypyridine; Et3N
3: TMSCl; phenol / CH2Cl2
View Scheme
(1S,4S,2'S)-(4-benzyloxymethyl-2-hydroxy-1-{2'-[4-methoxy-3-(3-methoxypropoxy)benzyl]-3-methylbutyl}-5-methylhexyl)carbamic acid tert-butyl ester

(1S,4S,2'S)-(4-benzyloxymethyl-2-hydroxy-1-{2'-[4-methoxy-3-(3-methoxypropoxy)benzyl]-3-methylbutyl}-5-methylhexyl)carbamic acid tert-butyl ester

(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
173334-57-1

(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 4 steps
1: 23 percent / H2 / Pd(OH)2/C
2: 38 percent / TPAP; NMMO
3: 65 percent / 2-hydroxypyridine; Et3N
4: TMSCl; phenol / CH2Cl2
View Scheme
isovanillin
621-59-0

isovanillin

(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
173334-57-1

(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 17 steps
1: 98 percent / K2CO3 / acetonitrile
2: NaBH4 / ethanol
3: PBr3 / CH2Cl2
4: 76 percent / LiHMDS / tetrahydrofuran
5: 81 percent / LiOH; H2O2
6: 95 percent / LAH / tetrahydrofuran
7: 97 percent / PPh3; NBS / CH2Cl2
8: 68 percent / n-BuLi
9: HCl / acetonitrile
10: Et3N
11: NaBH4 / ethanol
12: 89 percent / DMSO; ClC(O)C(O)Cl; Et3N / CH2Cl2
13: Mg
14: 23 percent / H2 / Pd(OH)2/C
15: 38 percent / TPAP; NMMO
16: 65 percent / 2-hydroxypyridine; Et3N
17: TMSCl; phenol / CH2Cl2
View Scheme
aminopivalinamide
324763-51-1

aminopivalinamide

(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
173334-57-1

(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 2 steps
1: 65 percent / 2-hydroxypyridine; Et3N
2: TMSCl; phenol / CH2Cl2
View Scheme
2-cyano-2-methylpropanamide
7505-93-3

2-cyano-2-methylpropanamide

(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
173334-57-1

(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 4 steps
1.1: LAH / tetrahydrofuran
1.2: Et3N
2.1: H2 / Pd()OH)2/C
3.1: 65 percent / 2-hydroxypyridine; Et3N
4.1: TMSCl; phenol / CH2Cl2
View Scheme
Multi-step reaction with 3 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
View Scheme
Multi-step reaction with 2 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
View Scheme
Multi-step reaction with 3 steps
1.1: ammonia / Raney nickel / methanol / 25 - 35 °C / Autoclave
1.2: 10 h / 60 - 65 °C / 5149.01 - 5884.58 Torr
2.1: triethylamine; 2-hydroxypyridin
3.1: hydrogenchloride / water; acetone / 20 °C
3.2: pH 8 - 9
View Scheme
(R)-4-benzyl-3-(3-methylbutyryl)oxazolidin-2-one
145589-03-3

(R)-4-benzyl-3-(3-methylbutyryl)oxazolidin-2-one

(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
173334-57-1

(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 14 steps
1: 76 percent / LiHMDS / tetrahydrofuran
2: 81 percent / LiOH; H2O2
3: 95 percent / LAH / tetrahydrofuran
4: 97 percent / PPh3; NBS / CH2Cl2
5: 68 percent / n-BuLi
6: HCl / acetonitrile
7: Et3N
8: NaBH4 / ethanol
9: 89 percent / DMSO; ClC(O)C(O)Cl; Et3N / CH2Cl2
10: Mg
11: 23 percent / H2 / Pd(OH)2/C
12: 38 percent / TPAP; NMMO
13: 65 percent / 2-hydroxypyridine; Et3N
14: TMSCl; phenol / CH2Cl2
View Scheme
Multi-step reaction with 9 steps
1: 50 percent / TiCl4 / CH2Cl2
2: 82 percent / LiOH; H2O2
3: 86 percent / LAH / tetrahydrofuran
4: 61 percent / PPh3; NBS / 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
Multi-step reaction with 13 steps
1.1: lithium hexamethyldisilazane / -78 °C / Inert atmosphere; Large scale
1.2: -78 °C / Inert atmosphere; Large scale
1.3: Inert atmosphere; Large scale
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere
3.1: triethylamine / toluene / 1.5 h / 0 - 20 °C / Inert atmosphere
4.1: sodium iodide / acetonitrile / 12 h / Inert atmosphere; Reflux
5.1: lithium hydride / N,N-dimethyl acetamide / 1 h / 60 °C / Inert atmosphere
5.2: 48 h / 60 °C / Inert atmosphere
6.1: dmap; triethylamine / 3 h / 20 °C / Inert atmosphere
7.1: trifluoroacetic acid / 1 h / 20 °C / Inert atmosphere
8.1: (R)-(-)-4,12-bis(diphenylphosphino)[2.2]paracyclophane(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; hydrogen; triethylamine / methanol / 24 h / 60 °C / 22502.3 Torr / Inert atmosphere; Large scale
9.1: diphenyl phosphoryl azide; triethylamine / toluene / 1 h / 80 °C / Inert atmosphere
9.2: 8 h / Inert atmosphere; Reflux
10.1: hydrogenchloride; water / ethanol / 48 h / 70 °C / Inert atmosphere
11.1: hydrogen; palladium 10% on activated carbon / methanol / 12 h / 20 °C / Inert atmosphere
11.2: 2 h / 20 °C / Inert atmosphere
12.1: 2-Ethylhexanoic acid / n-heptane / 8 h / 70 °C / Inert atmosphere
13.1: hydrogenchloride / dichloromethane / 3 h / -10 - 0 °C / Inert atmosphere
View Scheme
Multi-step reaction with 14 steps
1.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 2 h / -78 °C / Inert atmosphere
1.2: 20 h / -78 - 20 °C
2.1: water; dihydrogen peroxide; lithium hydroxide / tetrahydrofuran / 3 h / 0 - 20 °C
3.1: lithium aluminium tetrahydride / tetrahydrofuran / 6.5 h / 0 °C / Inert atmosphere; Reflux
4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1.5 h / 50 - 60 °C / Inert atmosphere
4.2: 20 °C
5.1: magnesium / tetrahydrofuran / 0.5 h / Inert atmosphere
5.2: -78 - 20 °C / Inert atmosphere
6.1: triethylamine; chlorotriethylstannane / 1,4-dioxane / 2 h / 0 °C
6.2: 20 °C
7.1: sodium periodate; ruthenium trichloride / acetonitrile / 0 - 20 °C
8.1: copper(II) sulfate / dichloromethane / 5 h / Reflux
9.1: boron trifluoride diethyl etherate / dichloromethane / 0.33 h / -78 - 20 °C
9.2: 5 h / 20 °C
10.1: diisobutylaluminium hydride / toluene / 2.5 h / -20 °C
11.1: magnesium / 0.5 h / Inert atmosphere
11.2: 3 h / -78 - 20 °C / Inert atmosphere
12.1: 10 wt% Pd(OH)2 on carbon; hydrogen / ethanol
13.1: 4-methylmorpholine N-oxide; tetrapropylammonium perruthennate / dichloromethane / 2 h / 20 °C / Inert atmosphere; Molecular sieve
14.1: triethylamine; 2-hydroxypyridin; hydrogenchloride / methanol / 80 °C
View Scheme
4-methoxy-3-(3-methoxypropoxy)benzaldehyde
172900-75-3

4-methoxy-3-(3-methoxypropoxy)benzaldehyde

(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
173334-57-1

(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 16 steps
1: NaBH4 / ethanol
2: PBr3 / CH2Cl2
3: 76 percent / LiHMDS / tetrahydrofuran
4: 81 percent / LiOH; H2O2
5: 95 percent / LAH / tetrahydrofuran
6: 97 percent / PPh3; NBS / CH2Cl2
7: 68 percent / n-BuLi
8: HCl / acetonitrile
9: Et3N
10: NaBH4 / ethanol
11: 89 percent / DMSO; ClC(O)C(O)Cl; Et3N / CH2Cl2
12: Mg
13: 23 percent / H2 / Pd(OH)2/C
14: 38 percent / TPAP; NMMO
15: 65 percent / 2-hydroxypyridine; Et3N
16: TMSCl; phenol / CH2Cl2
View Scheme
Multi-step reaction with 13 steps
1.1: sodium tetrahydroborate / tetrahydrofuran / 0 - 30 °C
1.2: pH 2
2.1: phosphorus tribromide / dichloromethane / 2.17 h / 0 - 5 °C
3.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -70 °C / Inert atmosphere
3.2: -70 - 5 °C
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: 12.5 h / 0 - 5 °C
8.1: water; lithium hydroxide / tetrahydrofuran; methanol / 26 h / 65 - 70 °C
8.2: 0.5 h / 0 - 5 °C
9.1: hydrogenchloride / 1,1-dichloroethane; water / 0 - 5 °C / pH 2.5
9.2: 14.25 h / 0 - 30 °C
10.1: N-Bromosuccinimide; phosphoric acid / water; tetrahydrofuran / 1.25 h / 0 - 5 °C
11.1: sodium azide / ethylene glycol / 20 h / 80 - 85 °C
12.1: triethylamine; 2-hydroxypyridin / 16 h / 85 - 90 °C
13.1: hydrogen; ethanolamine / palladium 10% on activated carbon / isopropyl alcohol / 3 h
View Scheme
Multi-step reaction with 10 steps
1.1: sodium tetrahydroborate / tetrahydrofuran / 0 - 30 °C
1.2: pH 2
2.1: phosphorus tribromide / dichloromethane / 2.17 h / 0 - 5 °C
3.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -70 °C / Inert atmosphere
3.2: -70 - 5 °C
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: 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: 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / 4 h / 75 - 80 °C
10.2: 15 h / 85 - 90 °C
10.3: 3 h
View Scheme
(R)-2-[4-methoxy-3-(3-methoxypropoxy)benzyl]-3-methylbutanol
172900-70-8

(R)-2-[4-methoxy-3-(3-methoxypropoxy)benzyl]-3-methylbutanol

(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
173334-57-1

(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 11 steps
1: 97 percent / PPh3; NBS / CH2Cl2
2: 68 percent / n-BuLi
3: HCl / acetonitrile
4: Et3N
5: NaBH4 / ethanol
6: 89 percent / DMSO; ClC(O)C(O)Cl; Et3N / CH2Cl2
7: Mg
8: 23 percent / H2 / Pd(OH)2/C
9: 38 percent / TPAP; NMMO
10: 65 percent / 2-hydroxypyridine; Et3N
11: TMSCl; phenol / CH2Cl2
View Scheme
Multi-step reaction with 7 steps
1: 70 percent / SOCl2; pyridine
2: Mg; BrCH2CH2Br / tetrahydrofuran / 20 °C
3: H2 / [Ru2Cl4((S)-BINAP)]NEt3 / methanol / 40 h / 40 °C / 37503 Torr
4: NEt3 / CH2Cl2
5: 85 percent / NaN3; 15-crown-6; DMPU
6: 59 percent / 2-OH-pyridine; NEt3
7: H2; aq. HCl / Pd/C / methanol
View Scheme
Multi-step reaction with 8 steps
1.1: N-chloro-succinimide; triphenylphosphine / dichloromethane / 5.5 h / -40 - 30 °C
2.1: magnesium; ethylene dibromide / tetrahydrofuran / 4.17 h / 63 - 68 °C / Inert atmosphere
2.2: 12.5 h / 0 - 5 °C
3.1: water; lithium hydroxide / tetrahydrofuran; methanol / 26 h / 65 - 70 °C
3.2: 0.5 h / 0 - 5 °C
4.1: hydrogenchloride / 1,1-dichloroethane; water / 0 - 5 °C / pH 2.5
4.2: 14.25 h / 0 - 30 °C
5.1: N-Bromosuccinimide; phosphoric acid / water; tetrahydrofuran / 1.25 h / 0 - 5 °C
6.1: sodium azide / ethylene glycol / 20 h / 80 - 85 °C
7.1: triethylamine; 2-hydroxypyridin / 16 h / 85 - 90 °C
8.1: hydrogen; ethanolamine / palladium 10% on activated carbon / isopropyl alcohol / 3 h
View Scheme
(R)-3-[4-methoxy-3-(3-methoxypropoxy)phenyl]-2-(1-methylethyl)propanoic acid
172900-71-9

(R)-3-[4-methoxy-3-(3-methoxypropoxy)phenyl]-2-(1-methylethyl)propanoic acid

(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
173334-57-1

(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 12 steps
1: 95 percent / LAH / tetrahydrofuran
2: 97 percent / PPh3; NBS / CH2Cl2
3: 68 percent / n-BuLi
4: HCl / acetonitrile
5: Et3N
6: NaBH4 / ethanol
7: 89 percent / DMSO; ClC(O)C(O)Cl; Et3N / CH2Cl2
8: Mg
9: 23 percent / H2 / Pd(OH)2/C
10: 38 percent / TPAP; NMMO
11: 65 percent / 2-hydroxypyridine; Et3N
12: TMSCl; phenol / CH2Cl2
View Scheme
Multi-step reaction with 8 steps
1: 90 percent / NaBH4; I2 / 96 h / 20 °C
2: 70 percent / SOCl2; pyridine
3: Mg; BrCH2CH2Br / tetrahydrofuran / 20 °C
4: H2 / [Ru2Cl4((S)-BINAP)]NEt3 / methanol / 40 h / 40 °C / 37503 Torr
5: NEt3 / CH2Cl2
6: 85 percent / NaN3; 15-crown-6; DMPU
7: 59 percent / 2-OH-pyridine; NEt3
8: H2; aq. HCl / Pd/C / methanol
View Scheme
Multi-step reaction with 9 steps
1.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere
1.2: 5.75 h / 0 - 30 °C
2.1: N-chloro-succinimide; triphenylphosphine / dichloromethane / 5.5 h / -40 - 30 °C
3.1: magnesium; ethylene dibromide / tetrahydrofuran / 4.17 h / 63 - 68 °C / Inert atmosphere
3.2: 12.5 h / 0 - 5 °C
4.1: water; lithium hydroxide / tetrahydrofuran; methanol / 26 h / 65 - 70 °C
4.2: 0.5 h / 0 - 5 °C
5.1: hydrogenchloride / 1,1-dichloroethane; water / 0 - 5 °C / pH 2.5
5.2: 14.25 h / 0 - 30 °C
6.1: N-Bromosuccinimide; phosphoric acid / water; tetrahydrofuran / 1.25 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
View Scheme
(2R)-3-methyl-2-[(phenylmethoxy)methyl]butan-1-ol
365541-75-9

(2R)-3-methyl-2-[(phenylmethoxy)methyl]butan-1-ol

(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
173334-57-1

(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 6 steps
1: 61 percent / PPh3; NBS / CH2Cl2
2: Mg
3: 23 percent / H2 / Pd(OH)2/C
4: 38 percent / TPAP; NMMO
5: 65 percent / 2-hydroxypyridine; Et3N
6: TMSCl; phenol / CH2Cl2
View Scheme
(4R)-3-{(2S)-3-methyl-1-oxo-2-[(phenylmethoxy)methyl]butyl}-4-(phenylmethyl)oxazolidin-2-one
365541-74-8

(4R)-3-{(2S)-3-methyl-1-oxo-2-[(phenylmethoxy)methyl]butyl}-4-(phenylmethyl)oxazolidin-2-one

(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
173334-57-1

(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 8 steps
1: 82 percent / LiOH; H2O2
2: 86 percent / LAH / tetrahydrofuran
3: 61 percent / PPh3; NBS / CH2Cl2
4: Mg
5: 23 percent / H2 / Pd(OH)2/C
6: 38 percent / TPAP; NMMO
7: 65 percent / 2-hydroxypyridine; Et3N
8: TMSCl; phenol / CH2Cl2
View Scheme
(2S)-(benzyloxymethyl)-3-methyl-butyl bromide
172901-00-7

(2S)-(benzyloxymethyl)-3-methyl-butyl bromide

(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
173334-57-1

(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
(2S)-3-methyl-2-[(phenylmethoxy)methyl]butanoic acid
656241-26-8

(2S)-3-methyl-2-[(phenylmethoxy)methyl]butanoic acid

(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
173334-57-1

(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 7 steps
1: 86 percent / LAH / tetrahydrofuran
2: 61 percent / PPh3; NBS / CH2Cl2
3: Mg
4: 23 percent / H2 / Pd(OH)2/C
5: 38 percent / TPAP; NMMO
6: 65 percent / 2-hydroxypyridine; Et3N
7: TMSCl; phenol / CH2Cl2
View Scheme
4-(bromomethyl)-1-methoxy-2-(3-methoxypropoxy)-benzene
172900-73-1

4-(bromomethyl)-1-methoxy-2-(3-methoxypropoxy)-benzene

(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
173334-57-1

(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 14 steps
1: 76 percent / LiHMDS / tetrahydrofuran
2: 81 percent / LiOH; H2O2
3: 95 percent / LAH / tetrahydrofuran
4: 97 percent / PPh3; NBS / CH2Cl2
5: 68 percent / n-BuLi
6: HCl / acetonitrile
7: Et3N
8: NaBH4 / ethanol
9: 89 percent / DMSO; ClC(O)C(O)Cl; Et3N / CH2Cl2
10: Mg
11: 23 percent / H2 / Pd(OH)2/C
12: 38 percent / TPAP; NMMO
13: 65 percent / 2-hydroxypyridine; Et3N
14: TMSCl; phenol / CH2Cl2
View Scheme
Multi-step reaction with 11 steps
1.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -70 °C / Inert atmosphere
1.2: -70 - 5 °C
2.1: dihydrogen peroxide; lithium hydroxide monohydrate / water; tetrahydrofuran / 0 - 30 °C
3.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere
3.2: 5.75 h / 0 - 30 °C
4.1: N-chloro-succinimide; triphenylphosphine / dichloromethane / 5.5 h / -40 - 30 °C
5.1: magnesium; ethylene dibromide / tetrahydrofuran / 4.17 h / 63 - 68 °C / Inert atmosphere
5.2: 12.5 h / 0 - 5 °C
6.1: water; lithium hydroxide / tetrahydrofuran; methanol / 26 h / 65 - 70 °C
6.2: 0.5 h / 0 - 5 °C
7.1: hydrogenchloride / 1,1-dichloroethane; water / 0 - 5 °C / pH 2.5
7.2: 14.25 h / 0 - 30 °C
8.1: N-Bromosuccinimide; phosphoric acid / water; tetrahydrofuran / 1.25 h / 0 - 5 °C
9.1: sodium azide / ethylene glycol / 20 h / 80 - 85 °C
10.1: triethylamine; 2-hydroxypyridin / 16 h / 85 - 90 °C
11.1: hydrogen; ethanolamine / palladium 10% on activated carbon / isopropyl alcohol / 3 h
View Scheme
Multi-step reaction with 10 steps
1.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -70 °C / Inert atmosphere
1.2: -70 - 5 °C
2.1: sodium tetrahydroborate / tetrahydrofuran / 0 - 15 °C
2.2: 11 h / 60 - 65 °C
3.1: N-chloro-succinimide; triphenylphosphine / dichloromethane / 5.5 h / -40 - 30 °C
4.1: magnesium; ethylene dibromide / tetrahydrofuran / 4.17 h / 63 - 68 °C / Inert atmosphere
4.2: 12.5 h / 0 - 5 °C
5.1: water; lithium hydroxide / tetrahydrofuran; methanol / 26 h / 65 - 70 °C
5.2: 0.5 h / 0 - 5 °C
6.1: hydrogenchloride / 1,1-dichloroethane; water / 0 - 5 °C / pH 2.5
6.2: 14.25 h / 0 - 30 °C
7.1: N-Bromosuccinimide; phosphoric acid / water; tetrahydrofuran / 1.25 h / 0 - 5 °C
8.1: sodium azide / ethylene glycol / 20 h / 80 - 85 °C
9.1: triethylamine; 2-hydroxypyridin / 16 h / 85 - 90 °C
10.1: hydrogen; ethanolamine / palladium 10% on activated carbon / isopropyl alcohol / 3 h
View Scheme
[4-methoxy-3-(3-methoxypropoxy)-phenyl]methanol
172900-74-2

[4-methoxy-3-(3-methoxypropoxy)-phenyl]methanol

(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
173334-57-1

(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 15 steps
1: PBr3 / CH2Cl2
2: 76 percent / LiHMDS / tetrahydrofuran
3: 81 percent / LiOH; H2O2
4: 95 percent / LAH / tetrahydrofuran
5: 97 percent / PPh3; NBS / CH2Cl2
6: 68 percent / n-BuLi
7: HCl / acetonitrile
8: Et3N
9: NaBH4 / ethanol
10: 89 percent / DMSO; ClC(O)C(O)Cl; Et3N / CH2Cl2
11: Mg
12: 23 percent / H2 / Pd(OH)2/C
13: 38 percent / TPAP; NMMO
14: 65 percent / 2-hydroxypyridine; Et3N
15: TMSCl; phenol / CH2Cl2
View Scheme
Multi-step reaction with 12 steps
1.1: phosphorus tribromide / dichloromethane / 2.17 h / 0 - 5 °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
View Scheme
Multi-step reaction with 10 steps
1.1: phosphorus tribromide / dichloromethane / 2.17 h / 0 - 5 °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: 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / 4 h / 75 - 80 °C
10.2: 15 h / 85 - 90 °C
10.3: 3 h
View Scheme
(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
172900-69-5

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene

(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
173334-57-1

(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 10 steps
1: 68 percent / n-BuLi
2: HCl / acetonitrile
3: Et3N
4: NaBH4 / ethanol
5: 89 percent / DMSO; ClC(O)C(O)Cl; Et3N / CH2Cl2
6: Mg
7: 23 percent / H2 / Pd(OH)2/C
8: 38 percent / TPAP; NMMO
9: 65 percent / 2-hydroxypyridine; Et3N
10: TMSCl; phenol / CH2Cl2
View Scheme
(2S,4S)-2-Amino-4-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-5-methyl-hexanoic acid ethyl ester
172900-99-1

(2S,4S)-2-Amino-4-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-5-methyl-hexanoic acid ethyl ester

(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
173334-57-1

(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 8 steps
1: Et3N
2: NaBH4 / ethanol
3: 89 percent / DMSO; ClC(O)C(O)Cl; Et3N / CH2Cl2
4: Mg
5: 23 percent / H2 / Pd(OH)2/C
6: 38 percent / TPAP; NMMO
7: 65 percent / 2-hydroxypyridine; Et3N
8: TMSCl; phenol / CH2Cl2
View Scheme
(2S,4S)-2-{[(tert-butoxy)carbonyl]amino}-4-[4-methoxy-3-(3-methoxypropoxy)benzyl]-5-methylhexan-1-ol
172900-82-2

(2S,4S)-2-{[(tert-butoxy)carbonyl]amino}-4-[4-methoxy-3-(3-methoxypropoxy)benzyl]-5-methylhexan-1-ol

(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
173334-57-1

(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 6 steps
1: 89 percent / DMSO; ClC(O)C(O)Cl; Et3N / CH2Cl2
2: Mg
3: 23 percent / H2 / Pd(OH)2/C
4: 38 percent / TPAP; NMMO
5: 65 percent / 2-hydroxypyridine; Et3N
6: TMSCl; phenol / CH2Cl2
View Scheme
ethyl (2S,4S)-2-{[(tert-butoxy)carbonyl]amino}-4-[4-methoxy-3-(3-methoxypropoxy)benzyl]-5-methylhexanoate
172900-76-4

ethyl (2S,4S)-2-{[(tert-butoxy)carbonyl]amino}-4-[4-methoxy-3-(3-methoxypropoxy)benzyl]-5-methylhexanoate

(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
173334-57-1

(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 7 steps
1: NaBH4 / ethanol
2: 89 percent / DMSO; ClC(O)C(O)Cl; Et3N / CH2Cl2
3: Mg
4: 23 percent / H2 / Pd(OH)2/C
5: 38 percent / TPAP; NMMO
6: 65 percent / 2-hydroxypyridine; Et3N
7: TMSCl; phenol / CH2Cl2
View Scheme
(2E)-but-2-enedioic acid
110-17-8

(2E)-but-2-enedioic acid

(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
173334-57-1

(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

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

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

Conditions
ConditionsYield
In ethanol; ethyl acetate93.6%
Stage #1: (2E)-but-2-enedioic acid; (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 In ethanol; acetonitrile at 20 - 50℃; for 0.333333h;
Stage #2: In ethanol; acetonitrile at 17 - 37℃; for 12.6667h; Product distribution / selectivity; aliskiren modification A;
In methanol at 40 - 45℃; Temperature; Solvent; Concentration;3.8 g
oxalic acid
144-62-7

oxalic acid

(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
173334-57-1

(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

(2S),(4S),(5S),(7S)-N-(3-amino-2,2-dimethyl-3-oxopropyl)-2,7-di(1-methylethyl)-4-hydroxy-5-amino-8-[4-methoxy-3-(3-methoxy-propoxy)phenyl]-octanamide hemioxalate

(2S),(4S),(5S),(7S)-N-(3-amino-2,2-dimethyl-3-oxopropyl)-2,7-di(1-methylethyl)-4-hydroxy-5-amino-8-[4-methoxy-3-(3-methoxy-propoxy)phenyl]-octanamide hemioxalate

Conditions
ConditionsYield
In water for 0.333333h;93.36%
succinic acid
110-15-6

succinic acid

(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
173334-57-1

(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

(2S),(4S),(5S),(7S)-N-(3-amino-2,2-dimethyl-3-oxopropyl)-2,7-di(1-methylethyl)-4-hydroxy-5-amino-8-[4-methoxy-3-(3-methoxy-propoxy)phenyl]-octanamide hemisuccinate

(2S),(4S),(5S),(7S)-N-(3-amino-2,2-dimethyl-3-oxopropyl)-2,7-di(1-methylethyl)-4-hydroxy-5-amino-8-[4-methoxy-3-(3-methoxy-propoxy)phenyl]-octanamide hemisuccinate

Conditions
ConditionsYield
In water for 0.25h;92.6%
citric acid
77-92-9

citric acid

(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
173334-57-1

(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

(2S),(4S),(5S),(7S)-N-(3-amino-2,2-dimethyl-3-oxopropyl)-2,7-di(1-methylethyl)-4-hydroxy-5-amino-8-[4-methoxy-3-(3-methoxy-propoxy)phenyl]-octanamide citrate

(2S),(4S),(5S),(7S)-N-(3-amino-2,2-dimethyl-3-oxopropyl)-2,7-di(1-methylethyl)-4-hydroxy-5-amino-8-[4-methoxy-3-(3-methoxy-propoxy)phenyl]-octanamide citrate

Conditions
ConditionsYield
In water for 0.5h; Product distribution / selectivity;92.37%
(2E)-but-2-enedioic acid
110-17-8

(2E)-but-2-enedioic acid

(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
173334-57-1

(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

(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
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;
L-Tartaric acid
87-69-4

L-Tartaric acid

(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
173334-57-1

(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

(2S),(4S),(5S),(7S)-N-(3-amino-2,2-dimethyl-3-oxopropyl)-2,7-di(1-methylethyl)-4-hydroxy-5-amino-8-[4-methoxy-3-(3-methoxy-propoxy)phenyl]-octanamide hemi(L-tartrate)

(2S),(4S),(5S),(7S)-N-(3-amino-2,2-dimethyl-3-oxopropyl)-2,7-di(1-methylethyl)-4-hydroxy-5-amino-8-[4-methoxy-3-(3-methoxy-propoxy)phenyl]-octanamide hemi(L-tartrate)

Conditions
ConditionsYield
In ethanol; acetonitrile at 20℃; for 0.0833333h; Product distribution / selectivity;72.85%
(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
173334-57-1

(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

(2S),(4S),(5S),(7S)-N-(3-amino-2,2-dimethyl-3-oxopropyl)-2,7-di(1-methylethyl)-4-hydroxy-5-amino-8-[4-methoxy-3-(3-methoxy-propoxy)phenyl]-octanamide phosphate
1327153-75-2

(2S),(4S),(5S),(7S)-N-(3-amino-2,2-dimethyl-3-oxopropyl)-2,7-di(1-methylethyl)-4-hydroxy-5-amino-8-[4-methoxy-3-(3-methoxy-propoxy)phenyl]-octanamide phosphate

Conditions
ConditionsYield
With phosphoric acid In water at 20℃; for 0.5h; Product distribution / selectivity;70.8%
acetic acid
64-19-7

acetic acid

(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
173334-57-1

(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

(2S),(4S),(5S),(7S)-N-(3-amino-2,2-dimethyl-3-oxopropyl)-2,7-di(1-methylethyl)-4-hydroxy-5-amino-8-[4-methoxy-3-(3-methoxy-propoxy)phenyl]-octanamide acetate
1327153-77-4

(2S),(4S),(5S),(7S)-N-(3-amino-2,2-dimethyl-3-oxopropyl)-2,7-di(1-methylethyl)-4-hydroxy-5-amino-8-[4-methoxy-3-(3-methoxy-propoxy)phenyl]-octanamide acetate

Conditions
ConditionsYield
In water for 0.5h;65%
(S)-Malic acid
97-67-6

(S)-Malic acid

(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
173334-57-1

(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

(2S),(4S),(5S),(7S)-N-(3-amino-2,2-dimethyl-3-oxopropyl)-2,7-di(1-methylethyl)-4-hydroxy-5-amino-8-[4-methoxy-3-(3-methoxy-propoxy)phenyl]-octanamide L-malate
1327153-72-9

(2S),(4S),(5S),(7S)-N-(3-amino-2,2-dimethyl-3-oxopropyl)-2,7-di(1-methylethyl)-4-hydroxy-5-amino-8-[4-methoxy-3-(3-methoxy-propoxy)phenyl]-octanamide L-malate

Conditions
ConditionsYield
In water for 0.5h; Product distribution / selectivity;63.3%
In ethanol; dichloromethane at 20℃; for 24h;
pentafluorophenol 4-nitroxybutyrate
838878-70-9

pentafluorophenol 4-nitroxybutyrate

(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
173334-57-1

(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

(2S,4S,5S,7S)-5-[4-(nitrooxy)butanoyl]amino-4-hydroxy-2-isopropyl-7-[4-methoxy-3-(3-methoxy-propopxy)-benzyl]-8-methyl-nonanoic acid (2-carbamoyl-2-methyl-propyl)-amide

(2S,4S,5S,7S)-5-[4-(nitrooxy)butanoyl]amino-4-hydroxy-2-isopropyl-7-[4-methoxy-3-(3-methoxy-propopxy)-benzyl]-8-methyl-nonanoic acid (2-carbamoyl-2-methyl-propyl)-amide

Conditions
ConditionsYield
With dmap; triethylamine In N,N-dimethyl-formamide at 0 - 20℃; for 4h;50%
4-(nitrooxy)butyl 4-nitrophenyl carbonate
935472-60-9

4-(nitrooxy)butyl 4-nitrophenyl carbonate

(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
173334-57-1

(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

(2S,4S,5S,7S)-5-[[[4-(nitrooxy)butyl]oxy]carbonyl]amino-4-hydroxy-2-isopropyl-7-[4-methoxy-3-(3-methoxy-propopxy)-benzyl]-8-methyl-nonanoic acid (2-carbamoyl-2-methyl-propyl)-amide

(2S,4S,5S,7S)-5-[[[4-(nitrooxy)butyl]oxy]carbonyl]amino-4-hydroxy-2-isopropyl-7-[4-methoxy-3-(3-methoxy-propopxy)-benzyl]-8-methyl-nonanoic acid (2-carbamoyl-2-methyl-propyl)-amide

Conditions
ConditionsYield
With dmap; triethylamine In N,N-dimethyl-formamide at 0 - 20℃; for 4h;50%
pentafluorophenol 4-nitroxybutyrate
838878-70-9

pentafluorophenol 4-nitroxybutyrate

(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
173334-57-1

(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

(2S,4S,5S,7S)-5-[4-(nitrooxy)butanoyl]amino-4-[4-(nitrooxy)butanoyl]oxy-2-isopropyl-7-[4-methoxy-3-(3-methoxy-propopxy)-benzyl]-8-methyl-nonanoic acid (2-carbamoyl-2-methyl-propyl)-amide

(2S,4S,5S,7S)-5-[4-(nitrooxy)butanoyl]amino-4-[4-(nitrooxy)butanoyl]oxy-2-isopropyl-7-[4-methoxy-3-(3-methoxy-propopxy)-benzyl]-8-methyl-nonanoic acid (2-carbamoyl-2-methyl-propyl)-amide

Conditions
ConditionsYield
With dmap; triethylamine In N,N-dimethyl-formamide at 0 - 20℃; for 4h;45%
[4-(nitrooxy)methyl]benzoic acid pentafluorophenyl ester
874446-96-5

[4-(nitrooxy)methyl]benzoic acid pentafluorophenyl ester

(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
173334-57-1

(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

(2S,4S,5S,7S)-5-[4-[(nitrooxy)methyl]benzoyl]amino-4-hydroxy-2-isopropyl-7-[4-methoxy-3-(3-methoxy-propopxy)-benzyl]-8-methyl-nonanoic acid (2-carbamoyl-2-methyl-propyl)-amide

(2S,4S,5S,7S)-5-[4-[(nitrooxy)methyl]benzoyl]amino-4-hydroxy-2-isopropyl-7-[4-methoxy-3-(3-methoxy-propopxy)-benzyl]-8-methyl-nonanoic acid (2-carbamoyl-2-methyl-propyl)-amide

Conditions
ConditionsYield
With dmap; scandium tris(trifluoromethanesulfonate) In N,N-dimethyl-formamide at 0 - 20℃; for 4h;30%
(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
173334-57-1

(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

2(S),4(S),5(S),7(S)-N-(3-amino-2,2-dimethyl-3-oxopropyl)-2,7-di(1-methylethyl)-4-hydroxy-5-amino-8-[4-methoxy-3-(3-methoxy-propoxy)phenyl]-octanamide, hydrogen sulfate salt of

2(S),4(S),5(S),7(S)-N-(3-amino-2,2-dimethyl-3-oxopropyl)-2,7-di(1-methylethyl)-4-hydroxy-5-amino-8-[4-methoxy-3-(3-methoxy-propoxy)phenyl]-octanamide, hydrogen sulfate salt of

Conditions
ConditionsYield
With sulfuric acid In water; acetonitrile at 0 - 5℃; for 10 - 48h;n/a
With sulfuric acid In water; acetonitrile at 0 - 5℃; for 11 - 49h;n/a

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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