Atorvastatin supplier | CasNO.134523-00-5

Name
Atorvastatin
EINECS 806-698-0
CAS No. 134523-00-5
Article Data35
CAS DataBase
Density 1.23 g/cm³
Solubility
Melting Point 176-178°C
Formula C₃₃H₃₅FN₂O₅
Boiling Point 722.2 °C at 760 mmHg
Molecular Weight 558.65
Flash Point 390.6 °C
Transport Information
Appearance
Safety 26-36
Risk Codes 20/21/22-36/37/38
Molecular Structure
Hazard Symbols Xn
Synonyms 1H-Pyrrole-1-heptanoicacid, 2-(4-fluorophenyl)-b,d-dihydroxy-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-,[R-(R*,R*)]-;(3R,5R)-7-[2-(4-Fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoicacid;(bR,dR)-2-(p-Fluorophenyl)-b,d-dihydroxy-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)pyrrole-1-heptanoicacid;Atorvastatin acid;Cardyl;Atorvastatin(base);
PSA 229.24000
LogP 10.10380

Synthetic route

: 134523-01-6
atorvastatin sodium

: 134523-00-5
atorvastatin

Conditions

Conditions	Yield
With sodium hydroxide at 60 - 70℃; pH=12-13;	95%
With hydrogenchloride In dichloromethane; water for 0.5h; Cooling with ice;	94%

: 134523-03-8
lipitor

: 134523-00-5
atorvastatin

Conditions

Conditions	Yield
With hydrogenchloride In tert-butyl methyl ether; water	92%
With hydrogenchloride In water; acetonitrile at 20℃; for 0.25h; pH=2.35 - 7;
With sodium hydrogen sulfate In water; ethyl acetate

: C7H15NO4

: 125971-96-2
2-[2-(4-fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxopentanoic acid phenylamide

: 134523-00-5
atorvastatin

Conditions

Conditions	Yield
With Trimethylacetic acid In toluene at 90℃; for 22h; Solvent; Temperature;	91%

: 134395-00-9
(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester

: 134523-00-5
atorvastatin

Conditions

Conditions	Yield
With sodium hydroxide In tetrahydrofuran; water at 20℃; Hydrolysis;
With methanol; potassium hydroxide; water
Stage #1: (3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester With methanol; sodium hydroxide; water In tert-butyl methyl ether for 2.08333 - 7.08333h; Heating / reflux; Stage #2: With hydrogenchloride pH=8.0 - 8.2;

: 124401-38-3
4-methyl-3-oxo-N-phenylpentanamide

: 134523-00-5
atorvastatin

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: β-alanine; glacial acetic acid / hexane / Heating 2: 3-ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromide; triethylamine / ethanol / Heating 3: pivalic acid / tetrahydrofuran; toluene; heptane / Heating 4: HCl / tetrahydrofuran; H2O / 20 °C 5: sodium hydroxide / H2O; tetrahydrofuran / 20 °C View Scheme

: 100-52-7
benzaldehyde

HI, I2: HI, I2

: 134523-00-5
atorvastatin

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: β-alanine; glacial acetic acid / hexane / Heating 2: 3-ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromide; triethylamine / ethanol / Heating 3: pivalic acid / tetrahydrofuran; toluene; heptane / Heating 4: HCl / tetrahydrofuran; H2O / 20 °C 5: sodium hydroxide / H2O; tetrahydrofuran / 20 °C View Scheme

: 125971-57-5
4-methyl-3-oxo-N-phenyl-2-(phenylmethylene)pentanamide

: 134523-00-5
atorvastatin

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 3-ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromide; triethylamine / ethanol / Heating 2: pivalic acid / tetrahydrofuran; toluene; heptane / Heating 3: HCl / tetrahydrofuran; H2O / 20 °C 4: sodium hydroxide / H2O; tetrahydrofuran / 20 °C View Scheme
Multi-step reaction with 3 steps 1.1: 3-ethyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazolium bromide; triethylamine / Reflux 2.1: Trimethylacetic acid / toluene; hexane; tetrahydrofuran / Reflux 3.1: hydrogenchloride / methanol / 0.08 h / 60 °C 3.2: 0.08 h / 60 °C View Scheme

: 125971-96-2
2-[2-(4-fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxopentanoic acid phenylamide

: 134523-00-5
atorvastatin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: pivalic acid / tetrahydrofuran; toluene; heptane / Heating 2: HCl / tetrahydrofuran; H2O / 20 °C 3: sodium hydroxide / H2O; tetrahydrofuran / 20 °C View Scheme

: 125971-95-1
tert-butyl (4R,6R)-6-{2-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)pyrrol-1-yl]ethyl}-2,2-dimethyl-1,3-dioxane-4-acetate

: 134523-00-5
atorvastatin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: HCl / tetrahydrofuran; H2O / 20 °C 2: sodium hydroxide / H2O; tetrahydrofuran / 20 °C View Scheme
Stage #1: tert-butyl (4R,6R)-6-{2-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)pyrrol-1-yl]ethyl}-2,2-dimethyl-1,3-dioxane-4-acetate With hydrogenchloride; water In tetrahydrofuran; methanol at 20℃; Stage #2: With sodium hydroxide; water In tetrahydrofuran; methanol at 0 - 20℃;
Stage #1: tert-butyl (4R,6R)-6-{2-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)pyrrol-1-yl]ethyl}-2,2-dimethyl-1,3-dioxane-4-acetate With hydrogenchloride; water In tetrahydrofuran at 25℃; for 8h; Stage #2: With sodium hydroxide; water In tetrahydrofuran for 8h; Stage #3: With phosphoric acid In water; ethyl acetate pH=4.0; Product distribution / selectivity;

: 62-53-3
aniline

Wang resin-bound styrene 4: Wang resin-bound styrene 4

: 134523-00-5
atorvastatin

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 96 percent / toluene / Heating 2: β-alanine; glacial acetic acid / hexane / Heating 3: 3-ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromide; triethylamine / ethanol / Heating 4: pivalic acid / tetrahydrofuran; toluene; heptane / Heating 5: HCl / tetrahydrofuran; H2O / 20 °C 6: sodium hydroxide / H2O; tetrahydrofuran / 20 °C View Scheme

: isobutyryl Meldrum's acid

: 134523-00-5
atorvastatin

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 96 percent / toluene / Heating 2: β-alanine; glacial acetic acid / hexane / Heating 3: 3-ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromide; triethylamine / ethanol / Heating 4: pivalic acid / tetrahydrofuran; toluene; heptane / Heating 5: HCl / tetrahydrofuran; H2O / 20 °C 6: sodium hydroxide / H2O; tetrahydrofuran / 20 °C View Scheme

: 1049684-97-0
((4R,6R)-6-(2-[2-(4-fluoro-phenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoyl-pyrrole-1-yl]-ethyl)-2-phenethyl-[1,3,2]dioxaborinane-4-yl)-acetic acid t-butyl ester

: 134523-00-5
atorvastatin

Conditions

Conditions	Yield
Stage #1: ((4R,6R)-6-(2-[2-(4-fluoro-phenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoyl-pyrrole-1-yl]-ethyl)-2-phenethyl-[1,3,2]dioxaborinane-4-yl)-acetic acid t-butyl ester With sodium hydroxide; water In ethyl acetate for 0.5h; Stage #2: With hydrogenchloride; water In ethyl acetate for 0.5h; pH=1 - ~ 2;

: 345891-62-5
(3R,5R)-methyl 7-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl)-3,5-dihydroxyheptanoate

A: (2Z,5S)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)pyrrol-1-yl]-5-hydroxyhept-2-enoic acid

B: 1105067-93-3
(2E,5S)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)pyrrol-1-yl]-5-hydroxyhept-2-enoic acid

C: 134523-00-5
atorvastatin

Conditions

Conditions	Yield
Stage #1: (3R,5R)-methyl 7-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl)-3,5-dihydroxyheptanoate With dmap; acetic anhydride; triethylamine In toluene at 60℃; for 2h; Stage #2: With sodium hydroxide In tetrahydrofuran; water; toluene at 25℃; for 16h; Further stages.;

...Expand

: 1331869-16-9
(R)-N,N-diallyl-5-(benzyloxy)-3-hydroxypentanethioamide

: 134523-00-5
atorvastatin

Conditions

Conditions	Yield
Multi-step reaction with 13 steps 1.1: 2,6-dimethylpyridine / dichloromethane / 3 h / 0 - 20 °C 2.1: diethyl ether / 4.5 h / 0 - 20 °C 3.1: tetrahydrofuran; diethyl ether / -78 °C 3.2: -78 °C 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3.5 h / 0 - 20 °C 5.1: sodium tetrahydroborate; diethyl methoxy borane / tetrahydrofuran; methanol / 10 h / -80 °C 6.1: toluene-4-sulfonic acid / acetone / 4 h / 20 °C 7.1: 20% palladium hydroxide on carbon; hydrogen / ethyl acetate / 24 h / 60 °C / 760.05 Torr 8.1: dmap; triethylamine / dichloromethane / 4 h / 0 - 20 °C 9.1: sodium azide / N,N-dimethyl-formamide / 6 h / 20 °C 10.1: water; triphenylphosphine / tetrahydrofuran / 2 h / 50 °C 11.1: Trimethylacetic acid / tetrahydrofuran; hexane; toluene / 30 h / 110 °C / Inert atmosphere 12.1: hydrogenchloride / tetrahydrofuran; methanol / 0.5 h / 0 - 20 °C 13.1: sodium hydroxide / tetrahydrofuran; water / 6 h / 0 - 20 °C 13.2: 20 °C View Scheme

Yield

Multi-step reaction with 13 steps
1.1: 2,6-dimethylpyridine / dichloromethane / 3 h / 0 - 20 °C
2.1: diethyl ether / 4.5 h / 0 - 20 °C
3.1: tetrahydrofuran; diethyl ether / -78 °C
3.2: -78 °C
4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3.5 h / 0 - 20 °C
5.1: sodium tetrahydroborate; diethyl methoxy borane / tetrahydrofuran; methanol / 10 h / -80 °C
6.1: toluene-4-sulfonic acid / acetone / 4 h / 20 °C
7.1: 20% palladium hydroxide on carbon; hydrogen / ethyl acetate / 24 h / 60 °C / 760.05 Torr
8.1: dmap; triethylamine / dichloromethane / 4 h / 0 - 20 °C
9.1: sodium azide / N,N-dimethyl-formamide / 6 h / 20 °C
10.1: water; triphenylphosphine / tetrahydrofuran / 2 h / 50 °C
11.1: Trimethylacetic acid / tetrahydrofuran; hexane; toluene / 30 h / 110 °C / Inert atmosphere
12.1: hydrogenchloride / tetrahydrofuran; methanol / 0.5 h / 0 - 20 °C
13.1: sodium hydroxide / tetrahydrofuran; water / 6 h / 0 - 20 °C
13.2: 20 °C
View Scheme

: 1347738-07-1
(R)-N,N-diallyl-5-(benzyloxy)-3-((tert-butyldimethylsilyl)oxy)pentanethioamide

: 134523-00-5
atorvastatin

Conditions

Conditions	Yield
Multi-step reaction with 12 steps 1.1: diethyl ether / 4.5 h / 0 - 20 °C 2.1: tetrahydrofuran; diethyl ether / -78 °C 2.2: -78 °C 3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3.5 h / 0 - 20 °C 4.1: sodium tetrahydroborate; diethyl methoxy borane / tetrahydrofuran; methanol / 10 h / -80 °C 5.1: toluene-4-sulfonic acid / acetone / 4 h / 20 °C 6.1: 20% palladium hydroxide on carbon; hydrogen / ethyl acetate / 24 h / 60 °C / 760.05 Torr 7.1: dmap; triethylamine / dichloromethane / 4 h / 0 - 20 °C 8.1: sodium azide / N,N-dimethyl-formamide / 6 h / 20 °C 9.1: water; triphenylphosphine / tetrahydrofuran / 2 h / 50 °C 10.1: Trimethylacetic acid / tetrahydrofuran; hexane; toluene / 30 h / 110 °C / Inert atmosphere 11.1: hydrogenchloride / tetrahydrofuran; methanol / 0.5 h / 0 - 20 °C 12.1: sodium hydroxide / tetrahydrofuran; water / 6 h / 0 - 20 °C 12.2: 20 °C View Scheme

Yield

Multi-step reaction with 12 steps
1.1: diethyl ether / 4.5 h / 0 - 20 °C
2.1: tetrahydrofuran; diethyl ether / -78 °C
2.2: -78 °C
3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3.5 h / 0 - 20 °C
4.1: sodium tetrahydroborate; diethyl methoxy borane / tetrahydrofuran; methanol / 10 h / -80 °C
5.1: toluene-4-sulfonic acid / acetone / 4 h / 20 °C
6.1: 20% palladium hydroxide on carbon; hydrogen / ethyl acetate / 24 h / 60 °C / 760.05 Torr
7.1: dmap; triethylamine / dichloromethane / 4 h / 0 - 20 °C
8.1: sodium azide / N,N-dimethyl-formamide / 6 h / 20 °C
9.1: water; triphenylphosphine / tetrahydrofuran / 2 h / 50 °C
10.1: Trimethylacetic acid / tetrahydrofuran; hexane; toluene / 30 h / 110 °C / Inert atmosphere
11.1: hydrogenchloride / tetrahydrofuran; methanol / 0.5 h / 0 - 20 °C
12.1: sodium hydroxide / tetrahydrofuran; water / 6 h / 0 - 20 °C
12.2: 20 °C
View Scheme

: CF3O3S(1-)*C25H42NO2SSi(1+)

: 134523-00-5
atorvastatin

Conditions

Conditions	Yield
Multi-step reaction with 11 steps 1.1: tetrahydrofuran; diethyl ether / -78 °C 1.2: -78 °C 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3.5 h / 0 - 20 °C 3.1: sodium tetrahydroborate; diethyl methoxy borane / tetrahydrofuran; methanol / 10 h / -80 °C 4.1: toluene-4-sulfonic acid / acetone / 4 h / 20 °C 5.1: 20% palladium hydroxide on carbon; hydrogen / ethyl acetate / 24 h / 60 °C / 760.05 Torr 6.1: dmap; triethylamine / dichloromethane / 4 h / 0 - 20 °C 7.1: sodium azide / N,N-dimethyl-formamide / 6 h / 20 °C 8.1: water; triphenylphosphine / tetrahydrofuran / 2 h / 50 °C 9.1: Trimethylacetic acid / tetrahydrofuran; hexane; toluene / 30 h / 110 °C / Inert atmosphere 10.1: hydrogenchloride / tetrahydrofuran; methanol / 0.5 h / 0 - 20 °C 11.1: sodium hydroxide / tetrahydrofuran; water / 6 h / 0 - 20 °C 11.2: 20 °C View Scheme

Yield

Multi-step reaction with 11 steps
1.1: tetrahydrofuran; diethyl ether / -78 °C
1.2: -78 °C
2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3.5 h / 0 - 20 °C
3.1: sodium tetrahydroborate; diethyl methoxy borane / tetrahydrofuran; methanol / 10 h / -80 °C
4.1: toluene-4-sulfonic acid / acetone / 4 h / 20 °C
5.1: 20% palladium hydroxide on carbon; hydrogen / ethyl acetate / 24 h / 60 °C / 760.05 Torr
6.1: dmap; triethylamine / dichloromethane / 4 h / 0 - 20 °C
7.1: sodium azide / N,N-dimethyl-formamide / 6 h / 20 °C
8.1: water; triphenylphosphine / tetrahydrofuran / 2 h / 50 °C
9.1: Trimethylacetic acid / tetrahydrofuran; hexane; toluene / 30 h / 110 °C / Inert atmosphere
10.1: hydrogenchloride / tetrahydrofuran; methanol / 0.5 h / 0 - 20 °C
11.1: sodium hydroxide / tetrahydrofuran; water / 6 h / 0 - 20 °C
11.2: 20 °C
View Scheme

: 1331869-20-5
(R)-tert-butyl 7-(benzyloxy)-5-((tert-butyldimethylsilyl)oxy)-3-oxoheptanoate

: 134523-00-5
atorvastatin

Conditions

Conditions	Yield
Multi-step reaction with 10 steps 1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3.5 h / 0 - 20 °C 2.1: sodium tetrahydroborate; diethyl methoxy borane / tetrahydrofuran; methanol / 10 h / -80 °C 3.1: toluene-4-sulfonic acid / acetone / 4 h / 20 °C 4.1: 20% palladium hydroxide on carbon; hydrogen / ethyl acetate / 24 h / 60 °C / 760.05 Torr 5.1: dmap; triethylamine / dichloromethane / 4 h / 0 - 20 °C 6.1: sodium azide / N,N-dimethyl-formamide / 6 h / 20 °C 7.1: water; triphenylphosphine / tetrahydrofuran / 2 h / 50 °C 8.1: Trimethylacetic acid / tetrahydrofuran; hexane; toluene / 30 h / 110 °C / Inert atmosphere 9.1: hydrogenchloride / tetrahydrofuran; methanol / 0.5 h / 0 - 20 °C 10.1: sodium hydroxide / tetrahydrofuran; water / 6 h / 0 - 20 °C 10.2: 20 °C View Scheme

Yield

Multi-step reaction with 10 steps
1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3.5 h / 0 - 20 °C
2.1: sodium tetrahydroborate; diethyl methoxy borane / tetrahydrofuran; methanol / 10 h / -80 °C
3.1: toluene-4-sulfonic acid / acetone / 4 h / 20 °C
4.1: 20% palladium hydroxide on carbon; hydrogen / ethyl acetate / 24 h / 60 °C / 760.05 Torr
5.1: dmap; triethylamine / dichloromethane / 4 h / 0 - 20 °C
6.1: sodium azide / N,N-dimethyl-formamide / 6 h / 20 °C
7.1: water; triphenylphosphine / tetrahydrofuran / 2 h / 50 °C
8.1: Trimethylacetic acid / tetrahydrofuran; hexane; toluene / 30 h / 110 °C / Inert atmosphere
9.1: hydrogenchloride / tetrahydrofuran; methanol / 0.5 h / 0 - 20 °C
10.1: sodium hydroxide / tetrahydrofuran; water / 6 h / 0 - 20 °C
10.2: 20 °C
View Scheme

: C18H26O5

: 134523-00-5
atorvastatin

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1.1: sodium tetrahydroborate; diethyl methoxy borane / tetrahydrofuran; methanol / 10 h / -80 °C 2.1: toluene-4-sulfonic acid / acetone / 4 h / 20 °C 3.1: 20% palladium hydroxide on carbon; hydrogen / ethyl acetate / 24 h / 60 °C / 760.05 Torr 4.1: dmap; triethylamine / dichloromethane / 4 h / 0 - 20 °C 5.1: sodium azide / N,N-dimethyl-formamide / 6 h / 20 °C 6.1: water; triphenylphosphine / tetrahydrofuran / 2 h / 50 °C 7.1: Trimethylacetic acid / tetrahydrofuran; hexane; toluene / 30 h / 110 °C / Inert atmosphere 8.1: hydrogenchloride / tetrahydrofuran; methanol / 0.5 h / 0 - 20 °C 9.1: sodium hydroxide / tetrahydrofuran; water / 6 h / 0 - 20 °C 9.2: 20 °C View Scheme

Yield

Multi-step reaction with 9 steps
1.1: sodium tetrahydroborate; diethyl methoxy borane / tetrahydrofuran; methanol / 10 h / -80 °C
2.1: toluene-4-sulfonic acid / acetone / 4 h / 20 °C
3.1: 20% palladium hydroxide on carbon; hydrogen / ethyl acetate / 24 h / 60 °C / 760.05 Torr
4.1: dmap; triethylamine / dichloromethane / 4 h / 0 - 20 °C
5.1: sodium azide / N,N-dimethyl-formamide / 6 h / 20 °C
6.1: water; triphenylphosphine / tetrahydrofuran / 2 h / 50 °C
7.1: Trimethylacetic acid / tetrahydrofuran; hexane; toluene / 30 h / 110 °C / Inert atmosphere
8.1: hydrogenchloride / tetrahydrofuran; methanol / 0.5 h / 0 - 20 °C
9.1: sodium hydroxide / tetrahydrofuran; water / 6 h / 0 - 20 °C
9.2: 20 °C
View Scheme

: C18H28O5

: 134523-00-5
atorvastatin

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1.1: toluene-4-sulfonic acid / acetone / 4 h / 20 °C 2.1: 20% palladium hydroxide on carbon; hydrogen / ethyl acetate / 24 h / 60 °C / 760.05 Torr 3.1: dmap; triethylamine / dichloromethane / 4 h / 0 - 20 °C 4.1: sodium azide / N,N-dimethyl-formamide / 6 h / 20 °C 5.1: water; triphenylphosphine / tetrahydrofuran / 2 h / 50 °C 6.1: Trimethylacetic acid / tetrahydrofuran; hexane; toluene / 30 h / 110 °C / Inert atmosphere 7.1: hydrogenchloride / tetrahydrofuran; methanol / 0.5 h / 0 - 20 °C 8.1: sodium hydroxide / tetrahydrofuran; water / 6 h / 0 - 20 °C 8.2: 20 °C View Scheme

Yield

Multi-step reaction with 8 steps
1.1: toluene-4-sulfonic acid / acetone / 4 h / 20 °C
2.1: 20% palladium hydroxide on carbon; hydrogen / ethyl acetate / 24 h / 60 °C / 760.05 Torr
3.1: dmap; triethylamine / dichloromethane / 4 h / 0 - 20 °C
4.1: sodium azide / N,N-dimethyl-formamide / 6 h / 20 °C
5.1: water; triphenylphosphine / tetrahydrofuran / 2 h / 50 °C
6.1: Trimethylacetic acid / tetrahydrofuran; hexane; toluene / 30 h / 110 °C / Inert atmosphere
7.1: hydrogenchloride / tetrahydrofuran; methanol / 0.5 h / 0 - 20 °C
8.1: sodium hydroxide / tetrahydrofuran; water / 6 h / 0 - 20 °C
8.2: 20 °C
View Scheme

: 1331869-21-6
tert-butyl 2-((4R,6R)-6-(2-(benzyloxy)ethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate

: 134523-00-5
atorvastatin

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1.1: 20% palladium hydroxide on carbon; hydrogen / ethyl acetate / 24 h / 60 °C / 760.05 Torr 2.1: dmap; triethylamine / dichloromethane / 4 h / 0 - 20 °C 3.1: sodium azide / N,N-dimethyl-formamide / 6 h / 20 °C 4.1: water; triphenylphosphine / tetrahydrofuran / 2 h / 50 °C 5.1: Trimethylacetic acid / tetrahydrofuran; hexane; toluene / 30 h / 110 °C / Inert atmosphere 6.1: hydrogenchloride / tetrahydrofuran; methanol / 0.5 h / 0 - 20 °C 7.1: sodium hydroxide / tetrahydrofuran; water / 6 h / 0 - 20 °C 7.2: 20 °C View Scheme

Yield

Multi-step reaction with 7 steps
1.1: 20% palladium hydroxide on carbon; hydrogen / ethyl acetate / 24 h / 60 °C / 760.05 Torr
2.1: dmap; triethylamine / dichloromethane / 4 h / 0 - 20 °C
3.1: sodium azide / N,N-dimethyl-formamide / 6 h / 20 °C
4.1: water; triphenylphosphine / tetrahydrofuran / 2 h / 50 °C
5.1: Trimethylacetic acid / tetrahydrofuran; hexane; toluene / 30 h / 110 °C / Inert atmosphere
6.1: hydrogenchloride / tetrahydrofuran; methanol / 0.5 h / 0 - 20 °C
7.1: sodium hydroxide / tetrahydrofuran; water / 6 h / 0 - 20 °C
7.2: 20 °C
View Scheme

: 1173184-84-3
tert-butyl 2-((4R,6R)-6-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate

: 134523-00-5
atorvastatin

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: dmap; triethylamine / dichloromethane / 4 h / 0 - 20 °C 2.1: sodium azide / N,N-dimethyl-formamide / 6 h / 20 °C 3.1: water; triphenylphosphine / tetrahydrofuran / 2 h / 50 °C 4.1: Trimethylacetic acid / tetrahydrofuran; hexane; toluene / 30 h / 110 °C / Inert atmosphere 5.1: hydrogenchloride / tetrahydrofuran; methanol / 0.5 h / 0 - 20 °C 6.1: sodium hydroxide / tetrahydrofuran; water / 6 h / 0 - 20 °C 6.2: 20 °C View Scheme

Yield

Multi-step reaction with 6 steps
1.1: dmap; triethylamine / dichloromethane / 4 h / 0 - 20 °C
2.1: sodium azide / N,N-dimethyl-formamide / 6 h / 20 °C
3.1: water; triphenylphosphine / tetrahydrofuran / 2 h / 50 °C
4.1: Trimethylacetic acid / tetrahydrofuran; hexane; toluene / 30 h / 110 °C / Inert atmosphere
5.1: hydrogenchloride / tetrahydrofuran; methanol / 0.5 h / 0 - 20 °C
6.1: sodium hydroxide / tetrahydrofuran; water / 6 h / 0 - 20 °C
6.2: 20 °C
View Scheme

: 1331869-22-7
tert-butyl 2-((4R,6R)-2,2-dimethyl-6-(2-(tosyloxy)ethyl)-1,3-dioxan-4-yl)acetate

: 134523-00-5
atorvastatin

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: sodium azide / N,N-dimethyl-formamide / 6 h / 20 °C 2.1: water; triphenylphosphine / tetrahydrofuran / 2 h / 50 °C 3.1: Trimethylacetic acid / tetrahydrofuran; hexane; toluene / 30 h / 110 °C / Inert atmosphere 4.1: hydrogenchloride / tetrahydrofuran; methanol / 0.5 h / 0 - 20 °C 5.1: sodium hydroxide / tetrahydrofuran; water / 6 h / 0 - 20 °C 5.2: 20 °C View Scheme

Yield

Multi-step reaction with 5 steps
1.1: sodium azide / N,N-dimethyl-formamide / 6 h / 20 °C
2.1: water; triphenylphosphine / tetrahydrofuran / 2 h / 50 °C
3.1: Trimethylacetic acid / tetrahydrofuran; hexane; toluene / 30 h / 110 °C / Inert atmosphere
4.1: hydrogenchloride / tetrahydrofuran; methanol / 0.5 h / 0 - 20 °C
5.1: sodium hydroxide / tetrahydrofuran; water / 6 h / 0 - 20 °C
5.2: 20 °C
View Scheme

: 125971-86-0, 125995-13-3
tert-butyl [(4R,6R)-6-aminoethyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate

: 134523-00-5
atorvastatin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: Trimethylacetic acid / tetrahydrofuran; hexane; toluene / 30 h / 110 °C / Inert atmosphere 2.1: hydrogenchloride / tetrahydrofuran; methanol / 0.5 h / 0 - 20 °C 3.1: sodium hydroxide / tetrahydrofuran; water / 6 h / 0 - 20 °C 3.2: 20 °C View Scheme

: 74-79-3
L-arginine

: 134523-00-5
atorvastatin

: atorvastatin arginine

Conditions

Conditions	Yield
In methanol; ethyl acetate at 25℃; for 1h;	96%
In ethanol; water at 75℃;

: 56-87-1
L-lysine

: 134523-00-5
atorvastatin

: atorvastatin lysine

Conditions

Conditions	Yield
In ethyl acetate at 25℃; for 24h;	95%
In dichloromethane at 25℃; for 24h;	72%
In isopropyl alcohol at 20℃; for 168h;
In ethanol; water at 75℃;

: 633-65-8
berberine chloride

: 134523-00-5
atorvastatin

: C33H34FN2O5(1-)*C20H18NO4(1+)

Conditions

Conditions	Yield
With sodium hydroxide In ethanol; water at 60 - 70℃; pH=7 - 8;	93%

: C50H104N2O24

: 134523-00-5
atorvastatin

: C116H170F2N6O32

Conditions

Conditions	Yield
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 30℃; for 9h;	91%

: 134523-00-5
atorvastatin

: [R-(R*,R*)]-2-(4-fluorophenyl)-β,δ-dihydroxy-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrole-1-heptanoic acid, calcium salt

Conditions

Conditions	Yield
With calcium hydroxide; water In methanol Product distribution / selectivity; Heating / reflux;	88%
With calcium hydroxide; water In acetone at 20 - 25℃; for 50.0333h; Product distribution / selectivity;	68%
With sodium hydroxide; calcium acetate In tert-butyl methyl ether; water; isopropyl alcohol for 24h; Product distribution / selectivity;
With sodium hydroxide; calcium chloride In water at 20 - 80℃; for 21.5h; Product distribution / selectivity;

: 134523-00-5
atorvastatin

: 1174332-81-0
1-((3R,5R)-3,5-dihydroxy-7-(hydroxyamino)-7-oxoheptyl)-5-(4-fluorophenyl)-2-isopropyl-N,4-diphenyl-7H-pyrrole-3-carboxamide

Conditions

Conditions	Yield
With hydroxylamine In tetrahydrofuran; water at 20℃; for 1h;	88%

: 929-59-9
3,6-dioxa-1,8-diaminooctane

: 134523-00-5
atorvastatin

: C72H82F2N6O10

Conditions

Conditions	Yield
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; for 6h;	88%

: 134523-00-5
atorvastatin

: 361543-12-6
PEODA13

: C92H122F2N6O20

Conditions

Conditions	Yield
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; for 12h;	88%

: C21H19BrNO4(1+)*Br(1-)

: 134523-00-5
atorvastatin

: C54H53FN3O9(1+)*Br(1-)

Conditions

Conditions	Yield
Stage #1: atorvastatin With sodium hydroxide In N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: C21H19BrNO4(1+)*Br(1-) In N,N-dimethyl-formamide at 70℃;	87%

: 68960-97-4
1,14-diamino-3,6,9,12-tetraoxatetradecane

: 134523-00-5
atorvastatin

: C76H90F2N6O12

Conditions

Conditions	Yield
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 35℃; for 12h;	86%

: 62-54-4
calcium acetate

: 134523-00-5
atorvastatin

: 134523-03-8
lipitor

Conditions

Conditions	Yield
Stage #1: calcium acetate; atorvastatin In water; acetonitrile at 44℃; for 1.25h; Stage #2: With sodium hydroxide In water at 30 - 70℃; for 9.5h; Product distribution / selectivity;	84.35%

: 923-27-3
D-lysine

: 134523-00-5
atorvastatin

: 609843-25-6
(3R,5R)-7-[3-phenyl-4-[(phenylamino)carbonyl]-2-(4-fluorophenyl)-5-(1-methyl-ethyl)-pyrrol-1-yl]-3,5-dihydroxy-heptanoic acid D-lysine salt

Conditions

Conditions	Yield
In ethyl acetate at 20℃; for 20h;	76%

: 70-54-2, 923-27-3, 6899-06-5, 60103-30-2, 60132-27-6, 56-87-1
2,6-diaminocaproic acid

: 134523-00-5
atorvastatin

: 609843-24-5
(3R,5R)-7-[3-phenyl-4-[(phenylamino)carbonyl]-2-(4-fluorophenyl)-5-(1-methyl-ethyl)-pyrrol-1-yl]-3,5-dihydroxy-heptanoic acid DL-lysine salt

Conditions

Conditions	Yield
In ethyl acetate	65%

: 70-26-8
L-ornithine

: 134523-00-5
atorvastatin

: (3R,5R)-7-[3-phenyl-4-[(phenylamino)carbonyl]-2-(4-fluorophenyl)-5-(1-methyl-ethyl)-pyrrol-1-yl]-3,5-dihydroxy-heptanoic acid L-ornithine salt

Conditions

Conditions	Yield
In ethyl acetate	47%

: 134523-00-5
atorvastatin

: 125995-03-1
atorvastatin lactone

Conditions

Conditions	Yield
In toluene at 60℃; for 40h;	46%
hydrogenchloride In toluene	n/a
In toluene for 4h; Product distribution / selectivity; Heating / reflux;
In hexane for 6h; Heating;	3.9 g

: 77-76-9
2,2-dimethoxy-propane

: 134523-00-5
atorvastatin

: 581772-29-4
2-((4R,6R)-6-(2-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl)ethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetic acid

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In acetone at 20℃; for 15h;	46%
In dichloromethane at 20℃;

: 134523-00-5
atorvastatin

: FITC-PEG3-NH2

: 1440755-31-6
1-((19R,21R)-1-(3',6'-dihydroxy-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthene]-5-ylamino)-19,21-dihydroxy-17-oxo-1-thioxo-6,9,12-trioxa-2,16-diazatricosan-23-yl)-5-(4-fluorophenyl)-2-isopropyl-N,4-diphenyl-1H-pyrrole-3-carboxamide

Conditions

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 36h;	41%

: 843660-59-3
1-(3-(2-(2-(3-aminopropoxy)ethoxy)ethoxy)propyl)-3-(3',6'-dihydroxy-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthen]-5-yl)thiourea

: 134523-00-5
atorvastatin

: 1440755-31-6
1-((19R,21R)-1-(3',6'-dihydroxy-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthene]-5-ylamino)-19,21-dihydroxy-17-oxo-1-thioxo-6,9,12-trioxa-2,16-diazatricosan-23-yl)-5-(4-fluorophenyl)-2-isopropyl-N,4-diphenyl-1H-pyrrole-3-carboxamide

Conditions

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 36h;	41%

: 67-56-1
methanol

: 134523-00-5
atorvastatin

A: 125995-03-1
atorvastatin lactone

B: 345891-62-5
(3R,5R)-methyl 7-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl)-3,5-dihydroxyheptanoate

Conditions

Conditions	Yield
With phosphoric acid In acetonitrile at 80℃; for 3h;	A 15.2 mg B 6.9 mg

...Expand

: 134523-00-5
atorvastatin

A: 5-(4-Fluoro-phenyl)-1-[2-((2R,4R)-4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-3-isopropyl-2-oxo-4-phenyl-2,3-dihydro-1H-pyrrole-3-carboxylic acid phenylamide

B: (3R,5R)-7-[3-(4-Fluoro-phenyl)-5-isopropyl-2-oxo-3-phenyl-4-phenylcarbamoyl-2,3-dihydro-pyrrol-1-yl]-3,5-dihydroxy-heptanoic acid

C: (3R,5R)-7-[5-(4-Fluoro-phenyl)-3-isopropyl-2-oxo-4-phenyl-3-phenylcarbamoyl-2,3-dihydro-pyrrol-1-yl]-3,5-dihydroxy-heptanoic acid

: 7-(9-fluoro-3-isopropyl-2-oxo-3-phenylcarbamoyl-2,3-dihydro-dibenzo[e,g]indol-1-yl)-3,5-dihydroxy-heptanoic acid

Conditions

Conditions	Yield
In acetone for 14h; Irradiation;

...Expand

Atorvastatin Chemical Properties

Molecular Structure of Atorvastatin (CAS NO.134523-00-5):

IUPAC Name: (3R,5R)-7-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-propan-2-ylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid
Empirical Formula: C₃₃H₃₅FN₂O₅
Molecular Weight: 558.6398
H bond acceptors: 7
H bond donors: 4
Freely Rotating Bonds: 14
Polar Surface Area: 70Å²
Index of Refraction: 1.602
Molar Refractivity: 155.21 cm³
Molar Volume: 451.9 cm³
Surface Tension: 45^.9 dyne/cm
Density: 1.23 g/cm³
Flash Point: 390.6 °C
Enthalpy of Vaporization: 110.74 kJ/mol
Boiling Point: 722.2 °C at 760 mmHg
Vapour Pressure: 6.84E-22 mmHg at 25 °C
Classification Code: Anticholesteremic Agents; Antilipemic Agents; Antimetabolites; Enzyme Inhibitors; Hydroxymethylglutaryl-CoA Reductase Inhibitors
InChI: InChI=1/C33H35FN2O5/c1-21(2)31-30(33(41)35-25-11-7-4-8-12-25)29(22-9-5-3-6-10-22)32(23-13-15-24(34)16-14-23)36(31)18-17-26(37)19-27(38)20-28(39)40/h3-16,21,26-27,37-38H,17-20H2,1-2H3,(H,35,41)(H,39,40)/t26-,27-/m1/s1
Smiles: c1(c(n(CC[C@H](C[C@H](CC(=O)O)O)O)c(c1C(Nc1ccccc1)=O)C(C)C)c1ccc(F)cc1)c1ccccc1

Atorvastatin History

Atorvastatin (CAS NO.134523-00-5) was first synthesized in 1985 by Bruce Roth while working at Parke-Davis Warner-Lambert Company (now Pfizer). With 2006 sales of US$12.9 billion, Lipitor is the largest-selling drug in the world. Lipitor is not the only statin, there are several other statins on the market.

Atorvastatin Uses

Atorvastatin is a member of the drug class known as statins, used for lowering blood cholesterol. It also stabilizes plaque and prevents strokes through anti-inflammatory and other mechanisms.

Atorvastatin Safety Profile

Hazard Codes: Harmful Xn
Risk Statements 20/21/22-36/37/38
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.

Atorvastatin Specification

Atorvastatin , with CAS number of 134523-00-5, can be called 1H-Pyrrole-1-heptanoicacid, 2-(4-fluorophenyl)-b,d-dihydroxy-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-,[R-(R*,R*)]- ; (bR,dR)-2-(p-Fluorophenyl)-b,d-dihydroxy-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)pyrrole-1-heptanoicacid ; (3R,5R)-7-[2-(4-Fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoicacid . Atorvastatin (CAS NO.134523-00-5) is used for lowering blood Cholesterol. It also stabilizes plaque and prevents strokes through anti-inflammatory and other mechanisms.

Product Name

Atorvastatin

Synthetic route

Atorvastatin Chemical Properties

Atorvastatin History

Atorvastatin Uses

Atorvastatin Safety Profile

Atorvastatin Specification

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