Lopinavir supplier | CasNO.192725-17-0

Name
Lopinavir
EINECS
CAS No. 192725-17-0
Article Data20
CAS DataBase
Density 1.163 g/cm³
Solubility
Melting Point 124-127 °C
Formula C₃₇H₄₈N₄O₅
Boiling Point 924.1 °C at 760 mmHg
Molecular Weight 628.812
Flash Point 512.7 °C
Transport Information
Appearance white crystalline solid
Safety
Risk Codes
Molecular Structure
Hazard Symbols Xi
Synonyms 1(2H)-Pyrimidineacetamide,N-[(1S,3S,4S)-4-[[(2,6-dimethylphenoxy)acetyl]amino]-3-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]tetrahydro-a-(1-methylethyl)-2-oxo-, (aS)- (9CI);1(2H)-Pyrimidineacetamide,N-[4-[[(2,6-dimethylphenoxy)acetyl]amino]-3-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]tetrahydro-a-(1-methylethyl)-2-oxo-, [1S-[1R*(R*),3R*,4R*]]-;A157378.0;ABT 378;Aluviran;Koletra;1(2H)-Pyrimidineacetamide,N-[(1S,3S,4S)-4-[[2-(2,6-dimethylphenoxy)acetyl]amino]-3-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]tetrahydro-a-(1-methylethyl)-2-oxo-, (aS)-;Intermediates of Lopinavir;
PSA 120.00000
LogP 4.39310

Synthetic route

: (2S,3S,5S)-2-amino-3-hydroxy-5-(2S-(1-tetrahydro-pyrimid-2-onyl)-3-methylbutanoyl)amino-1,6-diphenylhexane (S)-pyroglutamic acid salt

: C13H14N2O2

: 192725-17-0
lopinavir

Conditions

Conditions	Yield
In ethyl acetate at 25℃; for 8h; Solvent;	97%

: C28H40N4O2*C5H7NO3

: C13H14N2O2

: 192725-17-0
lopinavir

Conditions

Conditions	Yield
In dichloromethane at 25℃; for 8h; Solvent;	96%

: 224648-11-7
N-(2,6-dimethyl-phenyloxy acetyloxy)succinimide

: C28H40N4O2*C5H7NO3

: 192725-17-0
lopinavir

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 25℃; for 8h; Solvent;	96%

: (2S,3S,5S)-2-amino-3-hydroxy-5-(2S-(1-tetrahydro-pyrimid-2-onyl)-3-methylbutanoyl)amino-1,6-diphenylhexane (S)-pyroglutamic acid salt

: 224648-11-7
N-(2,6-dimethyl-phenyloxy acetyloxy)succinimide

: 192725-17-0
lopinavir

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 25℃; for 8h; Solvent;	96%

: 192800-77-4
2S-(1-tetrahydro-pyrimid-2-onyl)-3-methyl butanoyl chloride

: 192725-49-8
(2S,3S,5S)-2-(2,6-dimethylphenoxyacetyl)amino-3-hydroxy-5-amino-1,6-diphenylhexane

: 192725-17-0
lopinavir

Conditions

Conditions	Yield
With 1H-imidazole In ethyl acetate; N,N-dimethyl-formamide at 0 - 20℃; Reagent/catalyst; Inert atmosphere;	92%
With 1H-imidazole; dmap In ethyl acetate; N,N-dimethyl-formamide at 0 - 10℃; for 14h;

: C28H40N4O2*C5H7NO3

: C19H19NO5

: 192725-17-0
lopinavir

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 25℃; for 8h; Solvent;	92%

: (2S,3S,5S)-2-amino-3-hydroxy-5-(2S-(1-tetrahydro-pyrimid-2-onyl)-3-methylbutanoyl)amino-1,6-diphenylhexane (S)-pyroglutamic acid salt

: C19H19NO5

: 192725-17-0
lopinavir

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 25℃; for 8h; Solvent;	92%

: 192725-49-8
(2S,3S,5S)-2-(2,6-dimethylphenoxyacetyl)amino-3-hydroxy-5-amino-1,6-diphenylhexane

: 192725-50-1
(S)-tetrahydro-α-(1-methylethyl)-2-oxo-1(2H)-pyrimidineacetic acid

: 192725-17-0
lopinavir

Conditions

Conditions	Yield
Stage #1: (2S,3S,5S)-2-(2,6-dimethylphenoxyacetyl)amino-3-hydroxy-5-amino-1,6-diphenylhexane; (S)-tetrahydro-α-(1-methylethyl)-2-oxo-1(2H)-pyrimidineacetic acid With thionyl chloride In dichloromethane at 0℃; for 2h; Reflux; Stage #2: With triethylamine In dichloromethane at 0 - 20℃; for 5h;	90.1%
With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide	70%

: C28H40N4O2*C5H7NO3

: C18H15NO5

: 192725-17-0
lopinavir

Conditions

Conditions	Yield
With triethylamine In acetonitrile at 25℃; for 8h; Solvent;	89%

: (2S,3S,5S)-2-amino-3-hydroxy-5-(2S-(1-tetrahydro-pyrimid-2-onyl)-3-methylbutanoyl)amino-1,6-diphenylhexane (S)-pyroglutamic acid salt

: C18H15NO5

: 192725-17-0
lopinavir

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 25℃; for 8h; Solvent;	89%

: 192725-84-1
(S)-2-(3-Amino-propylamino)-3-methyl-butyric acid methyl ester

: 192725-17-0
lopinavir

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: LiOH 2: EDAC; HOBt View Scheme

: 192725-85-2
(S)-3-Methyl-2-(2-oxo-tetrahydro-pyrimidin-1-yl)-butyric acid methyl ester

: 192725-17-0
lopinavir

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: LiOH 2: EDAC; HOBt View Scheme

: 2-(3-tert-butoxycarbonylamino-propylamino)-3-methyl-butyric acid methyl ester

: 192725-17-0
lopinavir

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: trifluoroacetic acid 2: LiOH 3: EDAC; HOBt View Scheme

: 144163-85-9
(2S,3S,5S)-2-amino-3-hydroxy-5-(t-butyloxycarbonylamino)-1,6-diphenylhexane

: 192725-17-0
lopinavir

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: EDC 2: trifluoroacetic acid View Scheme
Multi-step reaction with 3 steps 1.1: thionyl chloride; N,N-dimethyl-formamide / ethyl acetate / 4 h / 50 °C 1.2: 5.25 h / 20 °C 2.1: trifluoroacetic acid / dichloromethane / 0 h / 0 - 25 °C / Inert atmosphere 3.1: triethylamine; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.33 h / 0 °C / Inert atmosphere 3.2: 12 h / 20 - 25 °C / Inert atmosphere View Scheme

: 156732-15-9
(2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-amino-1,6-diphenylhexane

: 192725-17-0
lopinavir

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: Pd(OH)2; HCO2NH4 2: EDC 3: trifluoroacetic acid View Scheme
Multi-step reaction with 3 steps 1.1: 1,1'-carbonyldiimidazole / ethyl acetate / 2 h / 15 - 20 °C 1.2: 4 h / 70 - 75 °C 2.1: 5%-palladium/activated carbon; ammonium formate / methanol / 2 h / 50 - 55 °C 3.1: sodium hydrogencarbonate / water; ethyl acetate / 0.5 h / 10 - 15 °C View Scheme

: 162849-93-6
(2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-(t-butyloxycarbonylamino)-1,6-diphenylhexane

: 192725-17-0
lopinavir

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: Pd(OH)2; HCO2NH4 2: EDC 3: trifluoroacetic acid View Scheme

: 192725-45-4
(2S,3S,5S)-2-(2,6-dimethylphenoxyacetyl)amino-3-hydroxy-5-(t-butyloxycarbonylamino)-1,6-diphenylhexane

: 192725-17-0
lopinavir

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: trifluoroacetic acid View Scheme

: (2S,3S,5S)-2-amino-3-hydroxy-5-(2S-(1-tetrahydro-pyrimid-2-onyl)-3-methylbutanoyl)amino-1,6-diphenylhexane (S)-pyroglutamic acid salt

: 20143-48-0
2,6-dimethylphenoxyacetyl chloride

: 192725-17-0
lopinavir

: 192726-05-9
(2S,3S,5S)-2-amino-3-hydroxy-5-(2S-(2-oxotetrahydropyrimidin-2-yl)-3-methylbutanoyl)amino-1,6-diphenylhexane

: 20143-48-0
2,6-dimethylphenoxyacetyl chloride

: 192725-17-0
lopinavir

: 192800-77-4
2S-(1-tetrahydro-pyrimid-2-onyl)-3-methyl butanoyl chloride

: 192725-17-0
lopinavir

Conditions

Conditions	Yield
Stage #1: (2S,3S,5S)-2-(2,6-dimethylphenoxyacetyl)amino-3-hydroxy-5-amino-1,6-diphenylhexane With 1H-imidazole In ethyl acetate at 20℃; Stage #2: 2S-(1-tetrahydro-pyrimid-2-onyl)-3-methyl butanoyl chloride In ethyl acetate; N,N-dimethyl-formamide at 0 - 20℃; for 13h;
Multi-step reaction with 4 steps 1: 1H-imidazole / ethyl acetate; N,N-dimethyl-formamide / 2 - 30 °C / Inert atmosphere 2: 5%-palladium/activated carbon; ammonium formate / methanol / 50 °C / Inert atmosphere 3: 1,4-dioxane / 1 h / 20 - 50 °C / Inert atmosphere 4: sodium hydrogencarbonate / ethyl acetate; water / 0.58 h / 20 °C / Inert atmosphere View Scheme

: 192725-49-8
(2S,3S,5S)-2-(2,6-dimethylphenoxyacetyl)amino-3-hydroxy-5-amino-1,6-diphenylhexane

: 192725-17-0
lopinavir

Conditions

Conditions	Yield
Stage #1: (2S,3S,5S)-2-(2,6-dimethylphenoxyacetyl)amino-3-hydroxy-5-amino-1,6-diphenylhexane With 1H-imidazole In ethyl acetate; N,N-dimethyl-formamide at 0 - 25℃; for 13h; Stage #2: With hydrogenchloride In water; ethyl acetate; N,N-dimethyl-formamide at 10 - 15℃;

: (2S,3S,5S)-2-amino-3-hydroxy-5-(2S-(1-tetrahydropyramid-2-only)-2-methylbutanoyl)-amino-1,6-diphenylhexane

: 20143-48-0
2,6-dimethylphenoxyacetyl chloride

: 192725-17-0
lopinavir

Conditions

Conditions	Yield
With sodium hydrogencarbonate In water; ethyl acetate at 20 - 25℃; for 1.16667h;

: 192725-50-1
(S)-tetrahydro-α-(1-methylethyl)-2-oxo-1(2H)-pyrimidineacetic acid

: 192725-17-0
lopinavir

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: thionyl chloride / tetrahydrofuran / 5.5 h / 4 - 20 °C / Inert atmosphere 2: 1H-imidazole / ethyl acetate; N,N-dimethyl-formamide / 2 - 30 °C / Inert atmosphere 3: 5%-palladium/activated carbon; ammonium formate / methanol / 50 °C / Inert atmosphere 4: 1,4-dioxane / 1 h / 20 - 50 °C / Inert atmosphere 5: sodium hydrogencarbonate / ethyl acetate; water / 0.58 h / 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1.1: 1,1'-carbonyldiimidazole / ethyl acetate / 2 h / 15 - 20 °C 1.2: 4 h / 70 - 75 °C 2.1: 5%-palladium/activated carbon; ammonium formate / methanol / 2 h / 50 - 55 °C 3.1: sodium hydrogencarbonate / water; ethyl acetate / 0.5 h / 10 - 15 °C View Scheme

Yield

Multi-step reaction with 5 steps
1: thionyl chloride / tetrahydrofuran / 5.5 h / 4 - 20 °C / Inert atmosphere
2: 1H-imidazole / ethyl acetate; N,N-dimethyl-formamide / 2 - 30 °C / Inert atmosphere
3: 5%-palladium/activated carbon; ammonium formate / methanol / 50 °C / Inert atmosphere
4: 1,4-dioxane / 1 h / 20 - 50 °C / Inert atmosphere
5: sodium hydrogencarbonate / ethyl acetate; water / 0.58 h / 20 °C / Inert atmosphere
View Scheme

Multi-step reaction with 3 steps
1.1: 1,1'-carbonyldiimidazole / ethyl acetate / 2 h / 15 - 20 °C
1.2: 4 h / 70 - 75 °C
2.1: 5%-palladium/activated carbon; ammonium formate / methanol / 2 h / 50 - 55 °C
3.1: sodium hydrogencarbonate / water; ethyl acetate / 0.5 h / 10 - 15 °C
View Scheme

: 72-18-4
L-valine

: 192725-17-0
lopinavir

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: lithium chloride; lithium hydroxide; aluminum oxide / water / 5 h / -20 - -10 °C / pH 9.5 - 10.2 / Inert atmosphere 2: sodium hydroxide / tetrahydrofuran / 2 h / 2 - 10 °C / Inert atmosphere 3: potassium tert-butylate / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere 4: thionyl chloride / tetrahydrofuran / 5.5 h / 4 - 20 °C / Inert atmosphere 5: 1H-imidazole / ethyl acetate; N,N-dimethyl-formamide / 2 - 30 °C / Inert atmosphere 6: 5%-palladium/activated carbon; ammonium formate / methanol / 50 °C / Inert atmosphere 7: 1,4-dioxane / 1 h / 20 - 50 °C / Inert atmosphere 8: sodium hydrogencarbonate / ethyl acetate; water / 0.58 h / 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 7 steps 1.1: potassium hydroxide / water / 2 h / 0 - 5 °C 2.1: sodium hydroxide / water / pH 9.5 - 10.5 3.1: ammonia; hydrogen / methanol / 10 h / 50 °C 4.1: sodium hydroxide / water / 98 - 100 °C 5.1: 1,1'-carbonyldiimidazole / ethyl acetate / 2 h / 15 - 20 °C 5.2: 4 h / 70 - 75 °C 6.1: 5%-palladium/activated carbon; ammonium formate / methanol / 2 h / 50 - 55 °C 7.1: sodium hydrogencarbonate / water; ethyl acetate / 0.5 h / 10 - 15 °C View Scheme

Yield

Multi-step reaction with 8 steps
1: lithium chloride; lithium hydroxide; aluminum oxide / water / 5 h / -20 - -10 °C / pH 9.5 - 10.2 / Inert atmosphere
2: sodium hydroxide / tetrahydrofuran / 2 h / 2 - 10 °C / Inert atmosphere
3: potassium tert-butylate / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere
4: thionyl chloride / tetrahydrofuran / 5.5 h / 4 - 20 °C / Inert atmosphere
5: 1H-imidazole / ethyl acetate; N,N-dimethyl-formamide / 2 - 30 °C / Inert atmosphere
6: 5%-palladium/activated carbon; ammonium formate / methanol / 50 °C / Inert atmosphere
7: 1,4-dioxane / 1 h / 20 - 50 °C / Inert atmosphere
8: sodium hydrogencarbonate / ethyl acetate; water / 0.58 h / 20 °C / Inert atmosphere
View Scheme

Multi-step reaction with 7 steps
1.1: potassium hydroxide / water / 2 h / 0 - 5 °C
2.1: sodium hydroxide / water / pH 9.5 - 10.5
3.1: ammonia; hydrogen / methanol / 10 h / 50 °C
4.1: sodium hydroxide / water / 98 - 100 °C
5.1: 1,1'-carbonyldiimidazole / ethyl acetate / 2 h / 15 - 20 °C
5.2: 4 h / 70 - 75 °C
6.1: 5%-palladium/activated carbon; ammonium formate / methanol / 2 h / 50 - 55 °C
7.1: sodium hydrogencarbonate / water; ethyl acetate / 0.5 h / 10 - 15 °C
View Scheme

: 126147-70-4
(2S)-3-Methyl-2-(phenoxycarbonyl)aminobutyric acid

: 192725-17-0
lopinavir

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: sodium hydroxide / tetrahydrofuran / 2 h / 2 - 10 °C / Inert atmosphere 2: potassium tert-butylate / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere 3: thionyl chloride / tetrahydrofuran / 5.5 h / 4 - 20 °C / Inert atmosphere 4: 1H-imidazole / ethyl acetate; N,N-dimethyl-formamide / 2 - 30 °C / Inert atmosphere 5: 5%-palladium/activated carbon; ammonium formate / methanol / 50 °C / Inert atmosphere 6: 1,4-dioxane / 1 h / 20 - 50 °C / Inert atmosphere 7: sodium hydrogencarbonate / ethyl acetate; water / 0.58 h / 20 °C / Inert atmosphere View Scheme

Yield

Multi-step reaction with 7 steps
1: sodium hydroxide / tetrahydrofuran / 2 h / 2 - 10 °C / Inert atmosphere
2: potassium tert-butylate / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere
3: thionyl chloride / tetrahydrofuran / 5.5 h / 4 - 20 °C / Inert atmosphere
4: 1H-imidazole / ethyl acetate; N,N-dimethyl-formamide / 2 - 30 °C / Inert atmosphere
5: 5%-palladium/activated carbon; ammonium formate / methanol / 50 °C / Inert atmosphere
6: 1,4-dioxane / 1 h / 20 - 50 °C / Inert atmosphere
7: sodium hydrogencarbonate / ethyl acetate; water / 0.58 h / 20 °C / Inert atmosphere
View Scheme

: C9H17ClN2O3

: 192725-17-0
lopinavir

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: potassium tert-butylate / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere 2: thionyl chloride / tetrahydrofuran / 5.5 h / 4 - 20 °C / Inert atmosphere 3: 1H-imidazole / ethyl acetate; N,N-dimethyl-formamide / 2 - 30 °C / Inert atmosphere 4: 5%-palladium/activated carbon; ammonium formate / methanol / 50 °C / Inert atmosphere 5: 1,4-dioxane / 1 h / 20 - 50 °C / Inert atmosphere 6: sodium hydrogencarbonate / ethyl acetate; water / 0.58 h / 20 °C / Inert atmosphere View Scheme

Yield

Multi-step reaction with 6 steps
1: potassium tert-butylate / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere
2: thionyl chloride / tetrahydrofuran / 5.5 h / 4 - 20 °C / Inert atmosphere
3: 1H-imidazole / ethyl acetate; N,N-dimethyl-formamide / 2 - 30 °C / Inert atmosphere
4: 5%-palladium/activated carbon; ammonium formate / methanol / 50 °C / Inert atmosphere
5: 1,4-dioxane / 1 h / 20 - 50 °C / Inert atmosphere
6: sodium hydrogencarbonate / ethyl acetate; water / 0.58 h / 20 °C / Inert atmosphere
View Scheme

: [1S]-N-[4-[bis(phenylmethyl)amino]-3-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]tetrahydro-R-(1-methylethyl)-2-oxo-1(2H)-pyrimidineacetamide

: 192725-17-0
lopinavir

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 5%-palladium/activated carbon; ammonium formate / methanol / 50 °C / Inert atmosphere 2: 1,4-dioxane / 1 h / 20 - 50 °C / Inert atmosphere 3: sodium hydrogencarbonate / ethyl acetate; water / 0.58 h / 20 °C / Inert atmosphere View Scheme

: [1S]-N-[4-amino-3-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]tetrahydro-R-(1-methylethyl)-2-oxo-1(2H)-pyrimidineacetamide

: 192725-17-0
lopinavir

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1,4-dioxane / 1 h / 20 - 50 °C / Inert atmosphere 2: sodium hydrogencarbonate / ethyl acetate; water / 0.58 h / 20 °C / Inert atmosphere View Scheme

: (2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-amino-1,6-diphenylhexane tartrate

: 192725-17-0
lopinavir

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydrogencarbonate / tert-butyl methyl ether; water / 1 h / 25 - 35 °C 1.2: 45 - 60 °C 2.1: ammonium formate; 5%-palladium/activated carbon / methanol / 50 - 55 °C 2.2: 1 h / 50 - 55 °C 3.1: sodium hydrogencarbonate / water; ethyl acetate / 1 h / 25 - 35 °C View Scheme

: 67746-43-4
dibenzyl N,N-diethylphosphoramidite

: 192725-17-0
lopinavir

: dibenzyl (1S,3S)-1-((1S)-1-{[(2,6-dimethylphenoxy)acetyl]amino}-2-phenylethyl)-3-{[(2S)-3-methyl-2-(2-oxotetrahydropyrimidin-1(2H)-yl)butanoyl]amino}-4-phenylbutyl phosphate

Conditions

Conditions	Yield
Stage #1: dibenzyl N,N-diethylphosphoramidite; lopinavir With 1H-tetrazole In tetrahydrofuran at 20℃; for 68h; Stage #2: With 3-chloro-benzenecarboperoxoic acid In tetrahydrofuran; dichloromethane at -45℃; for 0.5h;	90%

: 170436-73-4
4-{[bis(benzyloxy)phosphoryl]oxy}-3,3-dimethylbutanoic acid

: 192725-17-0
lopinavir

: (1S,3S)-1-((1S)-1-{[(2,6-dimethylphenoxy)acetyl]amino}-2-phenylethyl)3-{[(2S)-3-methyl-2-(2-oxotetrahydropyrimidin-1(2H)-yl)butanoyl]amino}-4-phenylbutyl 4-{[bis(benzyloxy)phosphoryl]oxy}-3,3-dimethylbutanoate

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 19h;	84%

: 67-68-5
dimethyl sulfoxide

: 192725-17-0
lopinavir

: 875435-49-7
(2S)-N-{(1S,3S,4S)-1-benzyl-4-{[(2,6-dimethylphenoxy)acetyl]amino}-3-[(methylthio)methoxy]-5-phenylpentyl}-3-methyl-2-(2-oxotetrahydropyrimidin-1(2H)-yl)butanamide

Conditions

Conditions	Yield
With acetic anhydride at 20℃; for 48h;	64%
With acetic anhydride; acetic acid at 20℃; for 48 - 72h; Product distribution / selectivity;	64%

: 352-93-2
diethyl sulphide

: 192725-17-0
lopinavir

: 875435-61-3
(2S)-N-{(1S,3S,4S)-1-benzyl-4-{[(2,6-dimethylphenoxy)acetyl]amino}-3-[1-(ethylthio)ethoxy]-5-phenylpentyl}-3-methyl-2-(2-oxotetrahydropyrimidin-1(2H)-yl)butanamide

Conditions

Conditions	Yield
With dibenzoyl peroxide In acetonitrile at 0 - 20℃; for 2.33333h;	61%
With dibenzoyl peroxide In acetonitrile at 0℃; for 3h; Product distribution / selectivity;	61%
Stage #1: diethyl sulphide With N-chloro-succinimide In tetrahydrofuran at -10℃; Stage #2: lopinavir With triethylamine In tetrahydrofuran at -10℃; for 1.5h; Product distribution / selectivity;

: 875435-99-7
dibenzyl 4-chloro-3,3-dimethyl-4-oxobutyl phosphate

: 192725-17-0
lopinavir

: (1S,3S)-1-((1S)-1-{[(2,6-dimethylphenoxy)acetyl]amino}-2-phenylethyl)-3-{[(2S)-3-methyl-2-(2-oxotetrahydropyrimidin-1(2H)-yl)butanoyl]amino}-4-phenylbutyl 4-{[bis(benzyloxy)phosphoryl]oxy}-2,2-dimethylbutanoate

Conditions

Conditions	Yield
With dmap In dichloromethane at 0 - 20℃; for 16h;	56%

: 67746-43-4
dibenzyl N,N-diethylphosphoramidite

: 192725-17-0
lopinavir

: C51H61N4O7P

Conditions

Conditions	Yield
With 1H-tetrazole In tetrahydrofuran at 20℃; for 68h;

Lopinavir Chemical Properties

IUPAC Name: (2S)-N-[(2S,4S,5S)-5-[[2-(2,6-Dimethylphenoxy)acetyl]amino]-4-hydroxy-1,6-diphenylhexan-2-yl]-3-methyl-2-(2-oxo-1,3-diazinan-1-yl)butanamide
Formula: C₃₇H₄₈N₄O₅
Molecular Weight: 628.8 g/mol
Molecular Structure of Lopinavir (CAS NO.192725-17-0):

Melting Point: 124-127 °C
Flash Point: 512.7 °C
Boiling Point: 924.1 °C at 760 mmHg
Density: 1.163 g/cm³
Enthalpy of Vaporization: 140.81 kJ/mol
Appearance: white crystalline solid
Index of Refraction: 1.577
Molar Refractivity: 179.17 cm³
Molar Volume: 540.4 cm³
Surface Tension: 49.4 dyne/cm
XLogP3-AA: 5.9
H-Bond Donor: 4
H-Bond Acceptor: 5
Rotatable Bond Count: 15
Tautomer Count: 8
Exact Mass: 628.362471
MonoIsotopic Mass: 628.362471
Topological Polar Surface Area: 120
Heavy Atom Count: 46
Product Categories: Anti-viral Compounds;Anti-virals;Intermediates & Fine Chemicals;Non-nucleoside Reverse Transcriptase;Pharmaceuticals

Lopinavir History

In an attempt to improve on the HIV resistance and serum protein-binding properties of the company's earlier protease inhibitor, ritonavir, Lopinavir was developed by Abbott. Abbott pursued a strategy of co-administering lopinavir with sub-therapeutic doses of ritonavir, and lopinavir is only marketed as a co-formulation with ritonavir. It is the first multi-drug capsule to contain a drug not available individually. Lopinavir/ritonavir was approved by the US FDA on 15 September 2000, and in Europe in April 2001. On June 26, 2016, Its patent will expire in the US. Abbott Laboratories was one of the earliest users of the Advanced Photon Source, a national synchrotron-radiation light source at Argonne National Laboratory. One of the early research projects undertaken at the Advanced Photon Source was the Human Immunodeficiency Virus. Using X-ray crystallography, researchers found the points of attack of the HIV protease inhibitors–agents that block the breakdown of proteins. Protease inhibitors stop HIV from making new copies of itself by blocking the last step in the process, when the virus attempts to replicate - and out of that discovery came the drug Kaletra.

Lopinavir Uses

Lopinavir (CAS NO.192725-17-0) is used as a selective HIV protease inhibitor. It is also used as an analogue of Ritonavir.

Lopinavir Specification

The chemical synonyms of Lopinavir (CAS NO.192725-17-0) is also named as (1S-(1R*(R*),3R*,4R*))-N-(4-(((2,6-Dimethylphenoxy)acetyl)amino)-3-hydroxy-5-phenyl-1-(phenylmethyl)pentyl)tetrahydro-alpha-(1-methylethyl)-2-oxo-1(2H)-pyrimidineacetamide ; (alphaS)-Tetrahydro-N-((alphaS)-alpha-((2S,3S)-2-hydroxy-4-phenyl-3-(2-(2,6-xylyloxy)acetamido)butyl)phenethyl)-alpha-isopropyl-2-oxo-1(2H)-pyrimidineacetamide ; A 157378.0 ; ABT 378 ; ABT-378 ; UNII-2494G1JF75 .

Product Name

Lopinavir

Synthetic route

Lopinavir Chemical Properties

Lopinavir History

Lopinavir Uses

Lopinavir Specification

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