Conditions | Yield |
---|---|
With triethylamine In 1-methyl-pyrrolidin-2-one at 50 - 55℃; Solvent; Reagent/catalyst; Temperature; Inert atmosphere; Large scale; | 78.1% |
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 25℃; for 24h; | 75% |
With tetrabutylammomium bromide; triethylamine In 1-methyl-pyrrolidin-2-one at 65 - 75℃; for 2h; Temperature; Reagent/catalyst; Solvent; | 57.5% |
7H-purin-6-ylamine
adefovir dipivoxyl
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 90 - 95℃; for 9h; Large scale; | 46.18% |
Conditions | Yield |
---|---|
With triethylamine In 1-methyl-pyrrolidin-2-one at 30 - 60℃; for 16h; Reagent/catalyst; | 32.6% |
adefovir dipivoxyl
Conditions | Yield |
---|---|
With acetic acid In methanol for 12h; Ambient temperature; Yield given; |
iodomethyl pivaloate
adefovir dipivoxyl
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: pyridine / 36 h / Ambient temperature 2: aq. AcOH / methanol / 12 h / Ambient temperature View Scheme |
N6-(4-monomethoxytrityl)-9-(2-phosphonomethoxyethyl)adenine
adefovir dipivoxyl
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: pyridine / 36 h / Ambient temperature 2: aq. AcOH / methanol / 12 h / Ambient temperature View Scheme |
N4-dimethylaminomethyledino-9-(2-phosphonomethoxyethyl)adenine di(pivaloyloxymethyl) ester
adefovir dipivoxyl
Conditions | Yield |
---|---|
Stage #1: N4-dimethylaminomethylideno-9-(2-phosphonomethoxyethyl)adinine di(pivaloyloxymethyl) ester With acetic acid In water at 25 - 55℃; for 3h; Stage #2: With triethylamine In water; ethyl acetate pH=7.5; | |
Stage #1: N4-dimethylaminomethylideno-9-(2-phosphonomethoxyethyl)adinine di(pivaloyloxymethyl) ester With water; acetic acid at 25 - 55℃; for 3h; Stage #2: With triethylamine In water; ethyl acetate pH=7.5; |
Chloromethyl pivalate
Adefovir
A
9-[2-({bis[(pivaloyloxy)methoxy]phosphinyl}methoxy)ethyl]-6-[(hydroxymethyl)amino]purine
B
adefovir dipivoxyl
Conditions | Yield |
---|---|
In dimethyl sulfoxide; triethylamine at 43℃; for 4h; | |
Stage #1: Chloromethyl pivalate; Adefovir With triethylamine In dimethyl sulfoxide at 40℃; for 5h; Stage #2: With water In dichloromethane; dimethyl sulfoxide at 10 - 20℃; for 0.0833333h; Product distribution / selectivity; |
adefovir dipivoxyl
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 25 - 85 °C 1.2: 20 h 2.1: water; hydrogen bromide / 4 h / 90 - 95 °C 2.2: 25 - 30 °C / pH 2.8 3.1: triethylamine; tetrabutylammomium bromide / ethyl acetate; N,N-dimethyl-formamide / 1 h / 25 - 35 °C 3.2: 25 - 35 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 16 h / 60 °C 2.1: ammonia / methanol / 14 h 3.1: magnesium 2-methylpropan-2-olate / N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere 3.2: 20 h / 35 °C / Inert atmosphere 4.1: sodium bromide; 1-methyl-pyrrolidin-2-one; chloro-trimethyl-silane / 12 h / 60 °C / Inert atmosphere 4.2: 6 h / 60 °C View Scheme | |
Multi-step reaction with 4 steps 1: triethylamine / acetonitrile / 14 h / 125 °C / Inert atmosphere 2: magnesium 2-methylpropan-2-olate / N,N-dimethyl-formamide / 12 h / 80 °C 3: chloro-trimethyl-silane / chlorobenzene / 10 h / 120 °C 4: triethylamine / 1-methyl-pyrrolidin-2-one / 16 h / 30 - 60 °C View Scheme |
[[2-(6-amino-9H-purine-9-yl)ethoxy]methyl]phosphonic acid diethyl ester
adefovir dipivoxyl
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: water; hydrogen bromide / 4 h / 90 - 95 °C 1.2: 25 - 30 °C / pH 2.8 2.1: triethylamine; tetrabutylammomium bromide / ethyl acetate; N,N-dimethyl-formamide / 1 h / 25 - 35 °C 2.2: 25 - 35 °C View Scheme |
Chloromethyl pivalate
[[2-(6-amino-9H-purine-9-yl)ethoxy]methyl]phosphonic acid diethyl ester
adefovir dipivoxyl
Conditions | Yield |
---|---|
Stage #1: [[2-(6-amino-9H-purine-9-yl)ethoxy]methyl]phosphonic acid diethyl ester With 1-methyl-pyrrolidin-2-one; chloro-trimethyl-silane; sodium bromide at 60℃; for 12h; Inert atmosphere; Stage #2: Chloromethyl pivalate With triethylamine at 60℃; for 6h; |
9-(2-hydroxyethyl)adenine
adefovir dipivoxyl
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: magnesium 2-methylpropan-2-olate / N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere 1.2: 20 h / 35 °C / Inert atmosphere 2.1: sodium bromide; 1-methyl-pyrrolidin-2-one; chloro-trimethyl-silane / 12 h / 60 °C / Inert atmosphere 2.2: 6 h / 60 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 5 °C / Large scale 1.2: 5 h / 5 °C / Large scale 2.1: trimethylsilyl bromide / acetonitrile / 3 h / 20 °C / Large scale 2.2: 2 h / Reflux; Large scale 3.1: triethylamine / 1-methyl-pyrrolidin-2-one / 2 h / 60 °C View Scheme | |
Multi-step reaction with 3 steps 1: magnesium 2-methylpropan-2-olate / N,N-dimethyl-formamide / 12 h / 80 °C 2: chloro-trimethyl-silane / chlorobenzene / 10 h / 120 °C 3: triethylamine / 1-methyl-pyrrolidin-2-one / 16 h / 30 - 60 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: magnesium 2-methylpropan-2-olate / N,N-dimethyl-formamide / 1 h / 78 - 82 °C 1.2: 78 - 82 °C 2.1: trimethylsilyl bromide / 80 - 85 °C 3.1: triethylamine / 1-methyl-pyrrolidin-2-one / 50 °C View Scheme |
adefovir dipivoxyl
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: ammonia / methanol / 14 h 2.1: magnesium 2-methylpropan-2-olate / N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere 2.2: 20 h / 35 °C / Inert atmosphere 3.1: sodium bromide; 1-methyl-pyrrolidin-2-one; chloro-trimethyl-silane / 12 h / 60 °C / Inert atmosphere 3.2: 6 h / 60 °C View Scheme |
6-Chloro-9-(β-hydroxyethylamino)purine
adefovir dipivoxyl
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran / -20 - 0 °C / Inert atmosphere 1.2: 48 h / 50 °C 2.1: trimethylhalosilane / acetonitrile / 20 °C / Inert atmosphere; Cooling with ice 3.1: N,N'-dicyclohexyl-4-morpholine carboxamidine; triethylamine / N,N-dimethyl-formamide / 12 h / 48 - 52 °C View Scheme |
6-chloro-9-(ethoxycarbonylmethyl)-9H-purine
adefovir dipivoxyl
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: methanol; sodium tetrahydroborate / 0 °C 2.1: sodium hydride / tetrahydrofuran / -20 - 0 °C / Inert atmosphere 2.2: 48 h / 50 °C 3.1: trimethylhalosilane / acetonitrile / 20 °C / Inert atmosphere; Cooling with ice 4.1: N,N'-dicyclohexyl-4-morpholine carboxamidine; triethylamine / N,N-dimethyl-formamide / 12 h / 48 - 52 °C View Scheme |
6-chloropurine
adefovir dipivoxyl
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: scandium tris(trifluoromethanesulfonate) / acetonitrile / 0.17 h / 20 °C 2.1: methanol; sodium tetrahydroborate / 0 °C 3.1: sodium hydride / tetrahydrofuran / -20 - 0 °C / Inert atmosphere 3.2: 48 h / 50 °C 4.1: trimethylhalosilane / acetonitrile / 20 °C / Inert atmosphere; Cooling with ice 5.1: N,N'-dicyclohexyl-4-morpholine carboxamidine; triethylamine / N,N-dimethyl-formamide / 12 h / 48 - 52 °C View Scheme |
Conditions | Yield |
---|---|
In ethyl acetate at 40℃; for 3h; Temperature; | 98% |
adefovir dipivoxyl
Conditions | Yield |
---|---|
With deuterium In tetrahydrofuran; cyclohexane at 55℃; under 1500.15 Torr; for 36h; Reagent/catalyst; Glovebox; | 96% |
Conditions | Yield |
---|---|
In acetone at 0 - 50℃; Product distribution / selectivity; | 90% |
In ethanol at 25℃; for 0.166667h; |
nicotinamide
adefovir dipivoxyl
adefovir dipivoxil:nicotinamide cocrystal
Conditions | Yield |
---|---|
In ethyl acetate at 20 - 70℃; for 25.25h; Product distribution / selectivity; | 80% |
Conditions | Yield |
---|---|
In tert-butyl methyl ether; acetone at 20℃; Product distribution / selectivity; Reflux; | 78% |
pivaloyl chloride
adefovir dipivoxyl
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; for 8h; Cooling with ice; | 76.13% |
adefovir dipivoxyl
9-{2-[O,O'-bis(pivaloyloxymethyl)thiophosphonomethoxy]ethyl}adenine
Conditions | Yield |
---|---|
With 2,4-bis(methylthio)-1,3-dithia-2,4-diphosphetane-2,4-disulfide In benzene at 0 - 80℃; for 2.5h; | 29% |
adefovir dipivoxyl
adefovir dipivoxil monohydrate
Conditions | Yield |
---|---|
With water In dichloromethane at 20 - 25℃; for 24h; | |
With water for 24h; |
Conditions | Yield |
---|---|
In ethyl acetate at 20 - 40℃; |
adefovir dipivoxyl
Adefovir
Conditions | Yield |
---|---|
With ethylenediaminetetraacetic acid; DL-dithiothreitol; water; magnesium chloride In aq. buffer at 37℃; for 1h; pH=7.5; Enzymatic reaction; |
Molecular Structure of Adefovir dipivoxil (CAS NO. 142340-99-6):
IUPAC Name: [2-(6-Aminopurin-9-yl)ethoxymethyl-(2,2-dimethylpropanoyloxymethoxy)phosphoryl]oxymethyl 2,2-dimethylpropanoate
Molecular Formula: C20H32N5O8P
Molecular Weight: 501.470541 g/mol
Index of Refraction: 1.569
Molar Refractivity: 120.96 cm3
Molar Volume: 369.1 cm3
Surface Tension: 51.1 dyne/cm
Density: 1.35 g/cm3
Flash Point: 341.5 °C
Enthalpy of Vaporization: 94.62 kJ/mol
Boiling Point: 641 °C at 760 mmHg
Vapour Pressure: 2.52E-16 mmHg at 25 °C
Melting Point: 98-102 °C
Storage Temp.: −20 °C
EINECS: 200-001-8
Product Categories: Active Pharmaceutical Ingredients; Adefovir
Adefovir dipivoxil can be obtained by two similar ways: 1) The reaction of adenine (I) with 2-(diisopropoxyphosphorylmethoxy)ethyl methanesulfonate (II) by means of cesium carbonate in DMF gives the expected condensation product (III), which is converted into the phosphonic acid (IV) by treatment with trimethylsilyl bromide in acetonitrile (1). Finally, this compound is condensed with chloromethyl pivalate (V) by means of N,N'-dicyclohexylmorpholine-4-carboxamidine in DMF. 2) The final condensation of the phosphonic acid (IV) can also be performed with iodomethyl pivalate (VI) in pyridine.
Safety Information of Adefovir dipivoxil (CAS NO. 142340-99-6):
Hazard Codes: Xn
Risk Statements: 20/21/22
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed
Safety Statements: 36/37
S36/37:Wear suitable protective clothing and gloves
Adefovir dipivoxil is also called (((2-(6-Amino-9H-purin-9-yl)ethoxy)methyl)phosphinylidene)bis(oxymethylene) 2,2-dimethylpropanoate ; ((2-(6-Amino-9H-purin-9-yl)ethoxy)methyl)phosphonic acid, diester with hydroxymethyl pivalate ; 9-(2-((-Bis((pivaloyloxy)methoxy)phosphinyl)methoxy)ethyl)adenine ; 9-(2-((Bis((pivaloyloxy)methoxy)phosphinyl)methoxy)ethyl)adenine ; Adefovir dipivoxil ; GS 840 ; GS-0840 ; Hepsera ; Preveon ; Propanoic acid, 2,2-dimethyl-, (((2-(6-amino-9H-purin-9-yl)ethoxy)methyl)phosphinylidene)bis(oxymethylene) ester ; UNII-U6Q8Z01514 .
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