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155206-00-1

Basic Information
CAS No.: 155206-00-1
Name: Bimatoprost
Molecular Structure:
Molecular Structure of 155206-00-1 (Bimatoprost)
Formula: C25H37NO4
Molecular Weight: 415.57
Synonyms: AGN 192024;5-Heptenamide,7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenyl-1-penten-1-yl]cyclopentyl]-N-ethyl-, (5Z)-;Lumigan;Prostamide;
EINECS: 642-890-9
Density: 1.145 g/cm3
Melting Point: 66-68°C
Boiling Point: 629.8 ºC at 760 mmHg
Flash Point: 334.7 ºC
Solubility: very soluble in ethyl alcohol and methyl alcohol and slightly soluble in water
Appearance: crystalline solid
Hazard Symbols:
Risk Codes:
Safety:
Transport Information:
PSA: 89.79000
LogP: 3.53780
Synthetic route
1240483-19-5

(Z)-7-((1R,2R,3R,5S)-3-(tert-butyldimethylsilyloxy)-2-((S,E)-3-(tert-butyldimethylsilyloxy)-5-phenylpent-1-enyl)-5-hydroxycyclopentyl)-N-ethylhept-5-enamide

155206-00-1

bimatoprost

Conditions
ConditionsYield
Stage #1: (Z)-7-((1R,2R,3R,5S)-3-(tert-butyldimethylsilyloxy)-2-((S,E)-3-(tert-butyldimethylsilyloxy)-5-phenylpent-1-enyl)-5-hydroxycyclopentyl)-N-ethylhept-5-enamide With hydrogenchloride; water In tetrahydrofuran at 20℃; for 18h;
Stage #2: In tetrahydrofuran pH=6.8; Aqueous phosphate buffer;
91%
Stage #1: (Z)-7-((1R,2R,3R,5S)-3-(tert-butyldimethylsilyloxy)-2-((S,E)-3-(tert-butyldimethylsilyloxy)-5-phenylpent-1-enyl)-5-hydroxycyclopentyl)-N-ethylhept-5-enamide With hydrogenchloride In tetrahydrofuran; water at 20℃; for 18h;
Stage #2: In tetrahydrofuran; water pH=6.8; Aqueous phosphate buffer;
91%
Stage #1: (Z)-7-((1R,2R,3R,5S)-3-(tert-butyldimethylsilyloxy)-2-((S,E)-3-(tert-butyldimethylsilyloxy)-5-phenylpent-1-enyl)-5-hydroxycyclopentyl)-N-ethylhept-5-enamide With ammonium hydrogen difluoride In tetrahydrofuran at 20 - 40℃; for 24h; Inert atmosphere;
Stage #2: With water In tetrahydrofuran; tert-butyl methyl ether Product distribution / selectivity;
80%
With hydrogenchloride; water In methanol at 15 - 20℃;
1430731-70-6

2,2-bis(hydroxymethyl)propyl (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenyl-1-pentenyl]cyclopentyl]-5-heptenoate

75-04-7

ethylamine

155206-00-1

bimatoprost

Conditions
ConditionsYield
In water at 20℃; for 72h;87.2%
1393740-68-5

(3aR,4R,5R,6aS)-4-[(3R)-(tert-butyldimethylsilyl)oxy-5-phenylpentyl]perhydrocyclopenta[b]furan-2,5-diol

155206-00-1

bimatoprost

Conditions
ConditionsYield
With hydrogenchloride; water In tetrahydrofuran at 20℃; for 22h;86%

2,2-bis(hydroxymethyl)propyl 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenyl-1-pentenyl]cyclopentyl]-5-heptenoate

75-04-7

ethylamine

A

1163135-95-2

(5E)-N-ethyl-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenyl-1-pentenyl]-cyclopentyl]hept-5-enamide

B

155206-00-1

bimatoprost

Conditions
ConditionsYield
In water at 20℃; for 72h; Overall yield = 87.2 %; Overall yield = 8.12 g;A n/a
B 83.7%
In water for 60h;A n/a
B 73%
75-04-7

ethylamine

38315-47-8

(Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-((S)-(E)-3-hydroxy-5-phenylpent-1-enyl)-cyclopentyl]hept-5-enoic acid methyl ester

155206-00-1

bimatoprost

Conditions
ConditionsYield
In methanol at 24 - 27℃; for 72h; Product distribution / selectivity;80%
In water at 20℃; for 60h;62%
In methanol; water at 90℃; for 45h;
856240-62-5

(3aR,4R,5R,6aS)-4-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]-hexahydro-2H-cyclopenta[b]furan-2,5-diol

1201226-16-5

(5-(ethylamino)-5-oxopentyl)triphenylphosphonium bromide

155206-00-1

bimatoprost

Conditions
ConditionsYield
Stage #1: (5-(ethylamino)-5-oxopentyl)triphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.666667h; Inert atmosphere;
Stage #2: (3aR,4R,5R,6aS)-hexahydro-4-[(1E,3S)-3-hydroxy-5-phenyl-1-penten-1-yl]-2H-cyclopenta[b]furan-2,5-diol In tetrahydrofuran at 20℃; for 4h; Reagent/catalyst; Temperature; Inert atmosphere;
80%
Stage #1: (3aR,4R,5R,6aS)-hexahydro-4-[(1E,3S)-3-hydroxy-5-phenyl-1-penten-1-yl]-2H-cyclopenta[b]furan-2,5-diol With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.666667h;
Stage #2: (5-(ethylamino)-5-oxopentyl)triphenylphosphonium bromide In tetrahydrofuran at 0℃;
65%
Stage #1: (5-(ethylamino)-5-oxopentyl)triphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.666667h; Inert atmosphere;
Stage #2: (3aR,4R,5R,6aS)-hexahydro-4-[(1E,3S)-3-hydroxy-5-phenyl-1-penten-1-yl]-2H-cyclopenta[b]furan-2,5-diol In tetrahydrofuran at 0 - 20℃; for 1h; Inert atmosphere;
41%
960056-50-2

(9S,11R,15S)-9,11,15-trihydroxy-17-phenyl-18,19,20-trinor-5Z,13E-prostadienoate

75-04-7

ethylamine

155206-00-1

bimatoprost

Conditions
ConditionsYield
With water at 20℃; for 60h;80%
856240-52-3

(5Z)-N-ethyl-7-((1R,2R,3R,5S)-5-hydroxy-2-((3S,E)-5-phenyl-3-(tetrahydro-2H-pyran-2-yloxy)pent-1-enyl)-3-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl)hept-5-enamide

155206-00-1

bimatoprost

Conditions
ConditionsYield
With toluene-4-sulfonic acid In methanol at 20℃; for 2h;77.5%
With toluene-4-sulfonic acid In methanol at 20℃; for 2h;77.5%

C23H30O4

75-04-7

ethylamine

155206-00-1

bimatoprost

Conditions
ConditionsYield
With trimethylaluminum In tetrahydrofuran at 20 - 40℃; for 18h; Product distribution / selectivity;67.3%
107-10-8

propylamine

130209-76-6

15α-hydroxy-17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester

155206-00-1

bimatoprost

Conditions
ConditionsYield
In methanol at 90℃;62%
1194047-64-7

(S,E)-1-((1S,5R,6R,7R)-3-butyl-7-((Z)-7-(ethylamino)-7-oxohept-2-en-1-yl)-2,4-dioxa-3-borabicyclo[3.2.1]octan-6-yl)-5-phenylpent-1-en-3-yl 6-bromohexanoate

A

1194396-71-8

(1S,2E)-3-[(1R,2R,3S,5R)-2-[(2Z)-7-(ethylamino)-7-oxo-2-hepten-1-yl]-3,5-dihydroxycyclopentyl]-1-(2-phenylethyl)-2-propen-1-yl-hexanoic acid 6-(nitrooxy)ester

B

C31H46ClNO5

C

155206-00-1

bimatoprost

Conditions
ConditionsYield
With silver nitrate In acetonitrile at 20 - 25℃; for 38h;A n/a
B n/a
C 4.27%
856240-62-5

(3aR,4R,5R,6aS)-4-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]-hexahydro-2H-cyclopenta[b]furan-2,5-diol

A

1163135-95-2

(5E)-N-ethyl-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenyl-1-pentenyl]-cyclopentyl]hept-5-enamide

B

155206-00-1

bimatoprost

Conditions
ConditionsYield
With sodium hexamethyldisilazane

C28H40O6

75-04-7

ethylamine

155206-00-1

bimatoprost

Conditions
ConditionsYield
In dichloromethane at -10℃; for 2h; Inert atmosphere;

C26H36O7

75-04-7

ethylamine

155206-00-1

bimatoprost

Conditions
ConditionsYield
In dichloromethane at -10℃; for 2h;
1224443-45-1

bimataprost L-arginine salt

75-04-7

ethylamine

155206-00-1

bimatoprost

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran; N,N-dimethyl-formamide Product distribution / selectivity;
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran; N,N-dimethyl-formamide Product distribution / selectivity;
329313-36-2

(S)-tert-butyldimethyl(5-phenylpent-1-yn-3-yloxy)silane

155206-00-1

bimatoprost

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: Schwartz's reagent / tetrahydrofuran / 3 h / 20 °C / Darkness
1.2: -78 - -20 °C
1.3: 0.5 h / -78 °C
2.1: diisobutylaluminium hydride / toluene / 3 h / -78 °C
2.2: -50 °C
3.1: dmap; diisopropyl-carbodiimide / tetrahydrofuran / 24 h / 20 - 40 °C / Inert atmosphere
4.1: Grubbs catalyst first generation / dichloromethane / 18 h / 20 - 40 °C / Inert atmosphere
5.1: tetrabutyl ammonium fluoride; ammonium hydrogen difluoride / tetrahydrofuran / 24 h / 20 - 40 °C
6.1: trimethylaluminum / tetrahydrofuran / 18 h / 20 - 40 °C
View Scheme
Multi-step reaction with 6 steps
1.1: Schwartz's reagent / tetrahydrofuran / 3 h / 20 °C / Darkness
1.2: -78 - -20 °C
1.3: 0.5 h / -78 °C
2.1: L-Selectride / tetrahydrofuran / 6 h / -78 °C / Inert atmosphere
3.1: dmap; diisopropyl-carbodiimide / tetrahydrofuran / 24 h / 20 - 40 °C / Inert atmosphere
4.1: Grubbs catalyst first generation / dichloromethane / 18 h / 20 - 40 °C / Inert atmosphere
5.1: tetrahydrofuran / 27 h / 20 - 40 °C / Reflux; Inert atmosphere
6.1: ammonium hydrogen difluoride / tetrahydrofuran / 24 h / 20 - 40 °C / Inert atmosphere
View Scheme
Multi-step reaction with 6 steps
1.1: Schwartz's reagent / tetrahydrofuran / 3 h / 20 °C / Darkness
1.2: -78 - -20 °C
1.3: 0.5 h / -78 °C
2.1: L-Selectride / tetrahydrofuran / 6 h / -78 °C / Inert atmosphere
3.1: dmap; diisopropyl-carbodiimide / tetrahydrofuran / 24 h / 20 - 40 °C / Inert atmosphere
4.1: Grubbs catalyst first generation / dichloromethane / 18 h / 20 - 40 °C / Inert atmosphere
5.1: tetrabutyl ammonium fluoride; ammonium hydrogen difluoride / tetrahydrofuran / 24 h / 20 - 40 °C
6.1: trimethylaluminum / tetrahydrofuran / 18 h / 20 - 40 °C
View Scheme

C31H52O3Si2

155206-00-1

bimatoprost

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: diisobutylaluminium hydride / toluene / 3 h / -78 °C
1.2: -50 °C
2.1: dmap; diisopropyl-carbodiimide / tetrahydrofuran / 24 h / 20 - 40 °C / Inert atmosphere
3.1: Grubbs catalyst first generation / dichloromethane / 18 h / 20 - 40 °C / Inert atmosphere
4.1: tetrabutyl ammonium fluoride; ammonium hydrogen difluoride / tetrahydrofuran / 24 h / 20 - 40 °C
5.1: trimethylaluminum / tetrahydrofuran / 18 h / 20 - 40 °C
View Scheme
Multi-step reaction with 5 steps
1.1: diisobutylaluminium hydride / toluene / 3 h / -78 °C
1.2: -50 °C
2.1: dmap; diisopropyl-carbodiimide / tetrahydrofuran / 24 h / 20 - 40 °C / Inert atmosphere
3.1: Grubbs catalyst first generation / dichloromethane / 18 h / 20 - 40 °C / Inert atmosphere
4.1: tetrahydrofuran / 27 h / 20 - 40 °C / Reflux; Inert atmosphere
5.1: ammonium hydrogen difluoride / tetrahydrofuran / 24 h / 20 - 40 °C / Inert atmosphere
View Scheme
Multi-step reaction with 5 steps
1: L-Selectride / tetrahydrofuran / 6 h / -78 °C / Inert atmosphere
2: dmap; diisopropyl-carbodiimide / tetrahydrofuran / 24 h / 20 - 40 °C / Inert atmosphere
3: Grubbs catalyst first generation / dichloromethane / 18 h / 20 - 40 °C / Inert atmosphere
4: tetrahydrofuran / 27 h / 20 - 40 °C / Reflux; Inert atmosphere
5: ammonium hydrogen difluoride / tetrahydrofuran / 24 h / 20 - 40 °C / Inert atmosphere
View Scheme
Multi-step reaction with 5 steps
1: L-Selectride / tetrahydrofuran / 6 h / -78 °C / Inert atmosphere
2: dmap; diisopropyl-carbodiimide / tetrahydrofuran / 24 h / 20 - 40 °C / Inert atmosphere
3: Grubbs catalyst first generation / dichloromethane / 18 h / 20 - 40 °C / Inert atmosphere
4: tetrabutyl ammonium fluoride; ammonium hydrogen difluoride / tetrahydrofuran / 24 h / 20 - 40 °C
5: trimethylaluminum / tetrahydrofuran / 18 h / 20 - 40 °C
View Scheme

C31H54O3Si2

155206-00-1

bimatoprost

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: dmap; diisopropyl-carbodiimide / tetrahydrofuran / 24 h / 20 - 40 °C / Inert atmosphere
2: Grubbs catalyst first generation / dichloromethane / 18 h / 20 - 40 °C / Inert atmosphere
3: tetrabutyl ammonium fluoride; ammonium hydrogen difluoride / tetrahydrofuran / 24 h / 20 - 40 °C
4: trimethylaluminum / tetrahydrofuran / 18 h / 20 - 40 °C
View Scheme
Multi-step reaction with 4 steps
1: dmap; diisopropyl-carbodiimide / tetrahydrofuran / 24 h / 20 - 40 °C / Inert atmosphere
2: Grubbs catalyst first generation / dichloromethane / 18 h / 20 - 40 °C / Inert atmosphere
3: tetrahydrofuran / 27 h / 20 - 40 °C / Reflux; Inert atmosphere
4: ammonium hydrogen difluoride / tetrahydrofuran / 24 h / 20 - 40 °C / Inert atmosphere
View Scheme

C37H62O4Si2

155206-00-1

bimatoprost

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: Grubbs catalyst first generation / dichloromethane / 18 h / 20 - 40 °C / Inert atmosphere
2: tetrabutyl ammonium fluoride; ammonium hydrogen difluoride / tetrahydrofuran / 24 h / 20 - 40 °C
3: trimethylaluminum / tetrahydrofuran / 18 h / 20 - 40 °C
View Scheme
Multi-step reaction with 3 steps
1: Grubbs catalyst first generation / dichloromethane / 18 h / 20 - 40 °C / Inert atmosphere
2: tetrahydrofuran / 27 h / 20 - 40 °C / Reflux; Inert atmosphere
3: ammonium hydrogen difluoride / tetrahydrofuran / 24 h / 20 - 40 °C / Inert atmosphere
View Scheme

C35H58O4Si2

155206-00-1

bimatoprost

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: tetrabutyl ammonium fluoride; ammonium hydrogen difluoride / tetrahydrofuran / 24 h / 20 - 40 °C
2: trimethylaluminum / tetrahydrofuran / 18 h / 20 - 40 °C
View Scheme
Multi-step reaction with 2 steps
1: tetrahydrofuran / 27 h / 20 - 40 °C / Reflux; Inert atmosphere
2: ammonium hydrogen difluoride / tetrahydrofuran / 24 h / 20 - 40 °C / Inert atmosphere
View Scheme

C17H27IOSi

155206-00-1

bimatoprost

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: n-butyllithium / hexane; tert-butyl methyl ether / 2 h / -78 °C / Inert atmosphere
1.2: 0.75 h / -78 °C / Inert atmosphere
2.1: diisobutylaluminium hydride / toluene / 3 h / -78 °C
2.2: -50 °C
3.1: dmap; diisopropyl-carbodiimide / tetrahydrofuran / 24 h / 20 - 40 °C / Inert atmosphere
4.1: Grubbs catalyst first generation / dichloromethane / 18 h / 20 - 40 °C / Inert atmosphere
5.1: tetrabutyl ammonium fluoride; ammonium hydrogen difluoride / tetrahydrofuran / 24 h / 20 - 40 °C
6.1: trimethylaluminum / tetrahydrofuran / 18 h / 20 - 40 °C
View Scheme
Multi-step reaction with 6 steps
1.1: n-butyllithium / hexane; tert-butyl methyl ether / 2 h / -78 °C / Inert atmosphere
1.2: 0.75 h / -78 °C / Inert atmosphere
2.1: L-Selectride / tetrahydrofuran / 6 h / -78 °C / Inert atmosphere
3.1: dmap; diisopropyl-carbodiimide / tetrahydrofuran / 24 h / 20 - 40 °C / Inert atmosphere
4.1: Grubbs catalyst first generation / dichloromethane / 18 h / 20 - 40 °C / Inert atmosphere
5.1: tetrahydrofuran / 27 h / 20 - 40 °C / Reflux; Inert atmosphere
6.1: ammonium hydrogen difluoride / tetrahydrofuran / 24 h / 20 - 40 °C / Inert atmosphere
View Scheme
Multi-step reaction with 6 steps
1.1: n-butyllithium / hexane; tert-butyl methyl ether / 2 h / -78 °C / Inert atmosphere
1.2: 0.75 h / -78 °C / Inert atmosphere
2.1: L-Selectride / tetrahydrofuran / 6 h / -78 °C / Inert atmosphere
3.1: dmap; diisopropyl-carbodiimide / tetrahydrofuran / 24 h / 20 - 40 °C / Inert atmosphere
4.1: Grubbs catalyst first generation / dichloromethane / 18 h / 20 - 40 °C / Inert atmosphere
5.1: tetrabutyl ammonium fluoride; ammonium hydrogen difluoride / tetrahydrofuran / 24 h / 20 - 40 °C
6.1: trimethylaluminum / tetrahydrofuran / 18 h / 20 - 40 °C
View Scheme
Multi-step reaction with 6 steps
1.1: n-butyllithium / hexane; tert-butyl methyl ether / 2 h / -78 °C / Inert atmosphere
1.2: 0.75 h / -78 °C / Inert atmosphere
2.1: diisobutylaluminium hydride / toluene / 3 h / -78 °C
2.2: -50 °C
3.1: dmap; diisopropyl-carbodiimide / tetrahydrofuran / 24 h / 20 - 40 °C / Inert atmosphere
4.1: Grubbs catalyst first generation / dichloromethane / 18 h / 20 - 40 °C / Inert atmosphere
5.1: tetrahydrofuran / 27 h / 20 - 40 °C / Reflux; Inert atmosphere
6.1: ammonium hydrogen difluoride / tetrahydrofuran / 24 h / 20 - 40 °C / Inert atmosphere
View Scheme
98974-31-3

(R)-2-allyl-4-(tert-butyldimethylsilyloxy)cyclopent-2-enone

155206-00-1

bimatoprost

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: n-butyllithium / hexane; tert-butyl methyl ether / 2 h / -78 °C / Inert atmosphere
1.2: 0.75 h / -78 °C / Inert atmosphere
2.1: diisobutylaluminium hydride / toluene / 3 h / -78 °C
2.2: -50 °C
3.1: dmap; diisopropyl-carbodiimide / tetrahydrofuran / 24 h / 20 - 40 °C / Inert atmosphere
4.1: Grubbs catalyst first generation / dichloromethane / 18 h / 20 - 40 °C / Inert atmosphere
5.1: tetrabutyl ammonium fluoride; ammonium hydrogen difluoride / tetrahydrofuran / 24 h / 20 - 40 °C
6.1: trimethylaluminum / tetrahydrofuran / 18 h / 20 - 40 °C
View Scheme
Multi-step reaction with 6 steps
1.1: n-butyllithium / hexane; tert-butyl methyl ether / 2 h / -78 °C / Inert atmosphere
1.2: 0.75 h / -78 °C / Inert atmosphere
2.1: L-Selectride / tetrahydrofuran / 6 h / -78 °C / Inert atmosphere
3.1: dmap; diisopropyl-carbodiimide / tetrahydrofuran / 24 h / 20 - 40 °C / Inert atmosphere
4.1: Grubbs catalyst first generation / dichloromethane / 18 h / 20 - 40 °C / Inert atmosphere
5.1: tetrahydrofuran / 27 h / 20 - 40 °C / Reflux; Inert atmosphere
6.1: ammonium hydrogen difluoride / tetrahydrofuran / 24 h / 20 - 40 °C / Inert atmosphere
View Scheme
Multi-step reaction with 6 steps
1.1: n-butyllithium / hexane; tert-butyl methyl ether / 2 h / -78 °C / Inert atmosphere
1.2: 0.75 h / -78 °C / Inert atmosphere
2.1: L-Selectride / tetrahydrofuran / 6 h / -78 °C / Inert atmosphere
3.1: dmap; diisopropyl-carbodiimide / tetrahydrofuran / 24 h / 20 - 40 °C / Inert atmosphere
4.1: Grubbs catalyst first generation / dichloromethane / 18 h / 20 - 40 °C / Inert atmosphere
5.1: tetrabutyl ammonium fluoride; ammonium hydrogen difluoride / tetrahydrofuran / 24 h / 20 - 40 °C
6.1: trimethylaluminum / tetrahydrofuran / 18 h / 20 - 40 °C
View Scheme
17814-85-6

(4-carboxybutyl)triphenylphosphonium bromide

155206-00-1

bimatoprost

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium hexamethyldisilazane / tetrahydrofuran / 20 °C / Inert atmosphere
2.1: tetrahydrofuran / -10 °C / Inert atmosphere
2.2: 15 - 30 °C / Cooling
View Scheme
Multi-step reaction with 3 steps
1.1: potassium carbonate / acetone / 10 h / 20 °C
2.1: bromine / water / 60 h / 25 °C
3.1: potassium tert-butylate / tetrahydrofuran / 0.67 h / 0 °C
3.2: 0 °C
View Scheme
1240483-16-2

(3aR,4R,5R,6aS)-5-((tert-butyldimethylsilyl)oxy)-4-((S,E)-3-((tert-butyldimethylsilyl)oxy)-5-phenylpent-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-2-ol

41723-91-5

4-carboxybutyliden triphenylphosphorane sodium

75-04-7

ethylamine

155206-00-1

bimatoprost

Conditions
ConditionsYield
Stage #1: (3aR,4R,5R,6aS)-5-((tert-butyldimethylsilyl)oxy)-4-((S,E)-3-((tert-butyldimethylsilyl)oxy)-5-phenylpent-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-2-ol; 4-carboxybutyliden triphenylphosphorane sodium In tetrahydrofuran at -10℃; Inert atmosphere;
Stage #2: With water; ammonium chloride In tetrahydrofuran; n-heptane; ethyl acetate at 15 - 30℃; Cooling;
Stage #3: ethylamine Product distribution / selectivity;

(3aR,4R,5R,6aS)-4-((E)-3-hydroxy-5-phenylpent-1-enyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl biphenyl-4-carboxylate

155206-00-1

bimatoprost

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: potassium carbonate; methanol / 15 h / 20 °C
1.2: 4 h / 20 - 31 °C
1.3: 4 h / 20 °C / pH ~ 1
2.1: 1H-imidazole / dmap / N,N-dimethyl-formamide / 15 h / 20 °C
3.1: water; methanol / 0 - 20 °C / Resolution of diastereomers
4.1: diisobutylaluminium hydride / toluene / -40 °C / Inert atmosphere
4.2: 20 °C
5.1: tetrahydrofuran / -10 °C / Inert atmosphere
5.2: 15 - 30 °C / Cooling
View Scheme
1240483-15-1

(3aR,4R,5R,6aS)-5-((tert-butyldimethylsilyl)oxy)-4-((S,E)-3-((tert-butyldimethylsilyl)oxy)-5-phenylpent-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-2-one

155206-00-1

bimatoprost

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: diisobutylaluminium hydride / toluene / -40 °C / Inert atmosphere
1.2: 20 °C
2.1: tetrahydrofuran / -10 °C / Inert atmosphere
2.2: 15 - 30 °C / Cooling
View Scheme
Multi-step reaction with 5 steps
1.1: diisobutylaluminium hydride / dichloromethane; hexane / 0.5 h / -30 °C / Inert atmosphere
1.2: -30 °C
2.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere
2.2: 3.25 h / 0 - 20 °C
3.1: potassium carbonate / acetone / 18 h / 20 °C
4.1: water / tetrahydrofuran / 52 h / 20 °C
5.1: hydrogenchloride / water; tetrahydrofuran / 18 h / 20 °C
5.2: pH 6.8 / Aqueous phosphate buffer
View Scheme

(3aR,4R,5R,6aS)-5-hydroxy-4-((E)-3-hydroxy-5-phenylpent-1-enyl)hexahydro-2H-cyclopenta[b]furan-2-one

155206-00-1

bimatoprost

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 1H-imidazole / dmap / N,N-dimethyl-formamide / 15 h / 20 °C
2.1: water; methanol / 0 - 20 °C / Resolution of diastereomers
3.1: diisobutylaluminium hydride / toluene / -40 °C / Inert atmosphere
3.2: 20 °C
4.1: tetrahydrofuran / -10 °C / Inert atmosphere
4.2: 15 - 30 °C / Cooling
View Scheme

C30H50O4Si2

155206-00-1

bimatoprost

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: water; methanol / 0 - 20 °C / Resolution of diastereomers
2.1: diisobutylaluminium hydride / toluene / -40 °C / Inert atmosphere
2.2: 20 °C
3.1: tetrahydrofuran / -10 °C / Inert atmosphere
3.2: 15 - 30 °C / Cooling
View Scheme
1300092-89-0

(3aR,4R,5R,6aS)-4-((S,E)-3-((2-methoxyethoxy)methoxy)-5-phenylpent-1-enyl)hexahydro-2H-cyclopenta[b]furan-2,5-diol

155206-00-1

bimatoprost

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 25 °C / Inert atmosphere
1.2: 1.5 h / 25 °C / Inert atmosphere
1.3: pH 5
2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetone / 8 h / 25 °C / Inert atmosphere
3.1: water / 24 h / 25 °C
4.1: sodium iodide; cerium(III) chloride heptahydrate / acetonitrile / 2 h / 80 - 85 °C
View Scheme
4426-47-5

butylboronic acid

155206-00-1

bimatoprost

1194047-63-6

(Z)-7-[(1S,5R,6R,7R)-3-butyl-6-[((E,3S)-3-hydroxy-5-phenylpent-1-enyl)]-2,4-dioxa-3-borabicyclo[3.2.1]octan-7-yl]-N-ethylhept-5-enamide

Conditions
ConditionsYield
In dichloromethane at 42℃; for 1h; Product distribution / selectivity; Inert atmosphere;100%
In tert-butyl methyl ether at 40℃; for 1h; Solvent;
In tert-butyl methyl ether at 40℃; for 1h; Solvent; Temperature; Inert atmosphere;
123-62-6

propionic acid anhydride

155206-00-1

bimatoprost

1393740-64-1

15-propionyl-bimatoprost

Conditions
ConditionsYield
Stage #1: bimatoprost With butylboronic acid In dichloromethane for 0.666667h; Reflux;
Stage #2: propionic acid anhydride With dmap; triethylamine In dichloromethane at 20℃; Cooling with ice;
88%
75-36-5

acetyl chloride

155206-00-1

bimatoprost

1393740-67-4

15-acetyl-bimatoprost

Conditions
ConditionsYield
Stage #1: bimatoprost With butylboronic acid In dichloromethane for 4h; Reflux;
Stage #2: acetyl chloride With pyridine In dichloromethane at 0℃; for 3h;
76%
155206-00-1

bimatoprost

(S)-2-acetoxypropionic acid (1S,2R,3R,4R)-4-((S)-2-acetoxypropionyloxy)-3-[(E)-(S)-3-((S)-2-acetoxypropionyloxy)-5-phenylpent-1-enyl]-2-((Z)-6-ethylcarbamoylhex-2-enyl)cyclopentyl

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 30℃; for 2h; Inert atmosphere;72%
69739-34-0

t-butyldimethylsiyl triflate

155206-00-1

bimatoprost

1393740-68-5

(3aR,4R,5R,6aS)-4-[(3R)-(tert-butyldimethylsilyl)oxy-5-phenylpentyl]perhydrocyclopenta[b]furan-2,5-diol

Conditions
ConditionsYield
Stage #1: bimatoprost With butylboronic acid In dichloromethane for 0.666667h; Reflux;
Stage #2: t-butyldimethylsiyl triflate With 2,6-dimethylpyridine In dichloromethane at 20℃; Cooling with ice;
64%
155206-00-1

bimatoprost

1163135-96-3

(5Z)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E)-3-oxo-5-phenylpent-1-en-1-yl]cyc!opentyl}-N-ethylhept-5-enamide

Conditions
ConditionsYield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,4-dioxane; dichloromethane at 40℃; for 24h;63%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,4-dioxane at 20℃; Inert atmosphere;50%

(S)-2-((S)-2-{(S)-2-[(S)-2-((S)-2-acetoxypropionyloxy)propionyloxy]propionyloxy}propionyloxy)propionic acid

155206-00-1

bimatoprost

C59H81NO26

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 30℃; for 2h; Inert atmosphere;59%

(2S)‐2‐{[(2S)‐2‐(acetyloxy)propanoyl]oxy}propanoic acid

155206-00-1

bimatoprost

C41H57NO14

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 30℃; for 2h; Inert atmosphere;52%

(S)-2-{(S)-2-[(S)-2-((S)-2-acetoxypropionyloxy)propionyloxy]propionyloxy}propionic acid

155206-00-1

bimatoprost

C53H73NO22

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 30℃; for 2h; Inert atmosphere;47%

(2S)-2-{[(2S)-2-{[(2S)-2-(acetyloxy)propanoyl]oxy}propanoyl]oxy}propanoic acid

155206-00-1

bimatoprost

C47H65NO18

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 30℃; for 2h; Inert atmosphere;42%
1194047-73-8

4-(nitrooxy)butyl 4-chloro-4-oxobutanoate

155206-00-1

bimatoprost

1194047-48-7

(1R,2R,3R,4S)-3-[(2Z)-7-(ethylamino)-7-oxohept-2-en-1-yl]-4-hydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl 4-(nitrooxy)butyl butanedioate

Conditions
ConditionsYield
With DMAP resin (PS-DMAP) In dichloromethane at 0 - 20℃; for 72.3333h; Inert atmosphere;30%
935472-60-9

4-(nitrooxy)butyl 4-nitrophenyl carbonate

155206-00-1

bimatoprost

A

1194047-46-5

(1S,2E)-3-{(1R,2R,3S,5R)-2-[(2Z)-7-(ethylamino)-7-oxohept-2-en-1-yl]-3,5-dihydroxycyclopentyl}-1-(2-phenylethyl)prop-2-en-1-yl 4-(nitrooxy)butyl carbonate

B

1194047-45-4

(2R,3R)-3-[(2Z)-7-(ethylamino)-7-oxohept-2-en-1-yl]-4-hydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl 4-(nitrooxy)butyl carbonate

C

1194047-56-7

(1S,2E)-3-[(1R,2R,3S,5R)-2-[(2Z)-7-(ethylamino)-7-oxohept-2-en-1-yl]-3-hydroxy-5-({[4-(nitrooxy)butoxy]carbonyl}oxy)cyclopentyl]-1-(2-phenylethyl)prop-2-en-1-yl 4-(nitrooxy)butyl carbonate

D

1194047-57-8

(1R,3S,4R,5R)-4-[(2Z)-7-(ethylamino)-7-oxohept-2-en-1-yl]-5-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentane-1 ,3-diyl bis[4-(nitrooxy)butyl] biscarbonate

E

1194047-55-6

(1R,3S,4R,5R)-4-[(2Z)-7-(ethylamino)-7-oxohept-2-en-1-yl]-5-[(1E,3S)-3-({[4-(nitrooxy)butoxy]carbonyl}oxy)-5-phenylpent-1-en-1-yl]cyclopentane-1,3-diyl bis[4-(nitrooxy)butyl]biscarbonate

Conditions
ConditionsYield
With dmap In dichloromethane at 20℃; for 60h; Inert atmosphere;A 2%
B 15%
C 18%
D 4%
E 5%
37693-18-8

4-chlorobutyl chloroformate

155206-00-1

bimatoprost

1194047-69-2

4-chlorobutyl (2R,3R)-3-[(2Z)-7-(ethylamino)-7-oxohept-2-en-1-yl]-4-hydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl carbonate

Conditions
ConditionsYield
With dmap In dichloromethane at 20℃; for 72h; Inert atmosphere;15%
907625-06-3

6-(nitrooxy)hexanoyl chloride

155206-00-1

bimatoprost

A

1194047-41-0

(1R,2R,3R,4S)-3-[(2Z)-7-(ethylamino)-7-oxohept-2-en-1-yl]-4-hydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl 6-(nitrooxy)hexanoate

B

1194047-42-1

(1S,2R,3R,4R)-2-[(2Z)-7-(ethylamino)-7-oxohept-2-en-1-yl]-4-hydroxy-3-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl 6-(nitrooxy)hexanoate

C

1194047-44-3

(1S,2E)-3-[(1R,2R,3S,5R)-2-[(2Z)-7-(ethylamino)-7-oxohept-2-en-1-yl]-3-hydroxy-5-{[6-(nitrooxy)hexanoyl]oxy}cyclopentyl]-1-(2-phenylethyl)prop-2-en-1-yl 6-(nitrooxy)hexanoate

D

1194047-43-2

(1R,3S,4R,5R)-4-[(2Z)-7-(ethylamino)-7-oxohept-2-en-1-yl]-5-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentane-1,3-diyl bis[6-(nitrooxy)hexanoate]

Conditions
ConditionsYield
With DMAP resin (PS-DMAP) In dichloromethane at 0 - 20℃; for 18.3333h; Inert atmosphere;A 12.4%
B 1.7%
C n/a
D n/a
927-58-2

4-bromobutyroyl chloride

155206-00-1

bimatoprost

1194047-71-6

(1R,2R,3R,4S)-3-[(2Z)-7-(ethylamino)-7-oxohept-2-en-1-yl]-4-hydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl 4-bromobutanoate

Conditions
ConditionsYield
With dmap In dichloromethane at 0℃; for 72h; Inert atmosphere;6%
108-30-5

succinic acid anhydride

155206-00-1

bimatoprost

1043914-34-6

C29H41NO7

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 20℃; for 0.333333h;
With dmap; triethylamine In dichloromethane at 20℃; for 1h; Product distribution / selectivity;
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    Specifications CAS No.: 155206-00-1 Other Names: / MF: C25H37NO4 EINECS No.: / Place of Origin: Shaanxi, China (Mainland)

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Specification

1. Introduction of Bimatoprost
Bimatoprost is crystalline solid. The Product Categories of this chemical is Prostaglandins; Prostaglandin; Chiral Reagents; Intermediates & Fine Chemicals; Pharmaceuticals; Arachidonic Acid Cascade; Lipids in Cell Signaling. The Classification Code of Bimatoprost is Antiglaucoma agent; Antihypertensive Agents; Cardiovascular Agents; Lowers intraocular pressure [IOP] in patients with open angle glaucoma or ocular hypertension [synthetic prostamide analog]. It should be store at -20 °C. Bimatoprost is very soluble in ethanol and methanol, and slightly soluble in water.

2. Properties of Bimatoprost
Physical properties about Bimatoprost are:
(1)H bond acceptors: 5; (2)H bond donors: 4; (3)Freely Rotating Bonds: 15; (4)Index of Refraction: 1.591; (5)Molar Refractivity: 122.67 cm3; (6)Molar Volume: 362.8 cm3; (7)Surface Tension: 48 dyne/cm; (8)Density: 1.145 g/cm3; (9)Flash Point: 334.7 °C; (10)Enthalpy of Vaporization: 97.93 kJ/mol; (11)Boiling Point: 629.8 °C at 760 mmHg; (12)Vapour Pressure: 9.94E-17 mmHg at 25 °C.

3. Structure Descriptors of Bimatoprost
(1)Canonical SMILES: CCNC(=O)CCCC=CCC1C(CC(C1C=CC(CCC2=CC=CC=C2)O)O)O
(2)Isomeric SMILES: CCNC(=O)CCC/C=C\C[C@H]1[C@H](C[C@H]([C@@H]1/C=C/[C@H](CCC2=CC=CC=C2)O)O)O
(3)InChI: InChI=1S/C25H37NO4/c1-2-26-25(30)13-9-4-3-8-12-21-22(24(29)18-23(21)28)17-16-20(27)15-14-19-10-6-5-7-11-19/h3,5-8,10-11,16-17,20-24,27-29H,2,4,9,12-15,18H2,1H3,(H,26,30)/b8-3-,17-16+/t20-,21+,22+,23-,24+/m0/s1
(4)InChIKey: AQOKCDNYWBIDND-FTOWTWDKSA-N

4. Safety Information of Bimatoprost
WGK Germany: 3

5. Uses of Bimatoprost
Bimatoprost (CAS NO.155206-00-1) is used topically (as eye drops) to control the progression of glaucoma and in the management of ocular hypertension. As an antiglaucoma, Bimatoprost can be used to synthetic prostamide or structurally related to prostaglandin F2α. Usually, it has been used topically (as eye drops) to control the progression of glaucoma and in the management of ocular hypertension. It can be used in the cosmetic use. In 2008-2011, at least three case series suggested that bimatoprost has the ability to reduce adipose (fat) tissue.

6. Production of Bimatoprost
(3AR, 4R, 5R, 6AS)-six hydrogen-4-(3-oxygen-5-phenyl-1 e-pentenyl)-5-(p-phenyl butyryl oxygen base)-2 h-ring pentaerythritol and [b] furan-2-ketone can be used to manufacture the Bimatoprost. The detailed steps of it is:
By the reduction reaction, and then to restore the carbonyl group on the furan ring is hydroxy, the hydrolysis before and valeric triphenylphosphine to afford 7-(1R, 2R, 3R, 5S) -3,5-two hydroxy-2 -[(3S) -5-phenyl-3-[(tetrahydro-2-H-pyran-2-yl)-oxygen]-1E-pentenyl] cyclopentyl]-5Z-heptenoic acid. Hydrolysis stripped pentenyl the protecting group on the hydroxyl group of the side chain. Was dissolved in dimethyl formamide and then iodomethane, Cs2CO3 role methyl, and finally reaction with the aqueous solution of ethylamine to get this product.