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142340-99-6

Basic Information
CAS No.: 142340-99-6
Name: Adefovir dipivoxil
Molecular Structure:
Molecular Structure of 142340-99-6 (Adefovir dipivoxil)
Formula: C20H32N5O8P
Molecular Weight: 501.48
Synonyms: 9-(2-((-Bis((pivaloyloxy)methoxy)phosphinyl)methoxy)ethyl)adenine;Adefovir pivoxil;Bis(POM)-PMEA;Preveon;Propanoic acid,2,2-dimethyl-,[[[2-(6-amino- 9H-purin-9-yl)ethoxy]methyl]phosphinylidene]- bis(oxymethylene) ester;Hepsera (TN);[2-(6-aminopurin-9-yl)ethoxymethyl-(2,2-dimethylpropanoyloxymethoxy)phosphoryl]oxymethyl 2,2-dimethylpropanoate;Bis(pivaloyloxymethyl)-9-(2-phosphonylmethoxyethyl)adenine;Adefovir pivoxil (JAN);Phosphonyl Methoxy Ethyl Adenine;Adefovirdipivoxil;Adefovir dipivoxyl;
EINECS: 200-001-8
Density: 1.35 g/cm3
Melting Point: 98-102 °C
Boiling Point: 641 °C at 760 mmHg
Flash Point: 341.5 °C
Solubility:
Appearance: It has broad-spectrum antiviral activity
Hazard Symbols: IrritantXi
Risk Codes: 20/21/22
Safety: 36/37
Transport Information:
PSA: 176.79000
LogP: 3.28370
Synthetic route
18997-19-8

Chloromethyl pivalate

106941-25-7

Adefovir

142340-99-6

adefovir dipivoxyl

Conditions
ConditionsYield
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%

[[2-chloroethoxy]methyl]phosphonic acid bis(pivaloyloxymethyl) ester

73-24-5

7H-purin-6-ylamine

142340-99-6

adefovir dipivoxyl

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 90 - 95℃; for 9h; Large scale;46.18%

chloropentyl pivalate

106941-25-7

Adefovir

142340-99-6

adefovir dipivoxyl

Conditions
ConditionsYield
With triethylamine In 1-methyl-pyrrolidin-2-one at 30 - 60℃; for 16h; Reagent/catalyst;32.6%

2,2-Dimethyl-propionic acid (2,2-dimethyl-propionyloxymethoxy)-[2-(6-{[(4-methoxy-phenyl)-diphenyl-methyl]-amino}-purin-9-yl)-ethoxymethyl]-phosphinoyloxymethyl ester

142340-99-6

adefovir dipivoxyl

Conditions
ConditionsYield
With acetic acid In methanol for 12h; Ambient temperature; Yield given;
53064-79-2

iodomethyl pivaloate

142340-99-6

adefovir dipivoxyl

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyridine / 36 h / Ambient temperature
2: aq. AcOH / methanol / 12 h / Ambient temperature
View Scheme
153235-86-0

N6-(4-monomethoxytrityl)-9-(2-phosphonomethoxyethyl)adenine

142340-99-6

adefovir dipivoxyl

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyridine / 36 h / Ambient temperature
2: aq. AcOH / methanol / 12 h / Ambient temperature
View Scheme
922494-99-3

N4-dimethylaminomethyledino-9-(2-phosphonomethoxyethyl)adenine di(pivaloyloxymethyl) ester

142340-99-6

adefovir dipivoxyl

Conditions
ConditionsYield
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;
18997-19-8

Chloromethyl pivalate

106941-25-7

Adefovir

A

323201-04-3

9-[2-({bis[(pivaloyloxy)methoxy]phosphinyl}methoxy)ethyl]-6-[(hydroxymethyl)amino]purine

B

142340-99-6

adefovir dipivoxyl

Conditions
ConditionsYield
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;
Conditions
ConditionsYield
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
116384-53-3

[[2-(6-amino-9H-purine-9-yl)ethoxy]methyl]phosphonic acid diethyl ester

142340-99-6

adefovir dipivoxyl

Conditions
ConditionsYield
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
18997-19-8

Chloromethyl pivalate

116384-53-3

[[2-(6-amino-9H-purine-9-yl)ethoxy]methyl]phosphonic acid diethyl ester

142340-99-6

adefovir dipivoxyl

Conditions
ConditionsYield
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;
707-99-3

9-(2-hydroxyethyl)adenine

142340-99-6

adefovir dipivoxyl

Conditions
ConditionsYield
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

benzoic acid 2-(6-amino-purin-9-yl)-ethyl ester

142340-99-6

adefovir dipivoxyl

Conditions
ConditionsYield
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
1670-62-8

6-Chloro-9-(β-hydroxyethylamino)purine

142340-99-6

adefovir dipivoxyl

Conditions
ConditionsYield
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
56791-59-4

6-chloro-9-(ethoxycarbonylmethyl)-9H-purine

142340-99-6

adefovir dipivoxyl

Conditions
ConditionsYield
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
87-42-3

6-chloropurine

142340-99-6

adefovir dipivoxyl

Conditions
ConditionsYield
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
110-16-7

maleic acid

142340-99-6

adefovir dipivoxyl

adefovir dipivoxil maleate

Conditions
ConditionsYield
In ethyl acetate at 40℃; for 3h; Temperature;98%
142340-99-6

adefovir dipivoxyl

C20H30(2)H2N5O8P

Conditions
ConditionsYield
With deuterium In tetrahydrofuran; cyclohexane at 55℃; under 1500.15 Torr; for 36h; Reagent/catalyst; Glovebox;96%
81-07-2

saccharin

142340-99-6

adefovir dipivoxyl

1403836-42-9

adefovir dipivoxil:saccharin salt

Conditions
ConditionsYield
In acetone at 0 - 50℃; Product distribution / selectivity;90%
In ethanol at 25℃; for 0.166667h;
98-92-0

nicotinamide

142340-99-6

adefovir dipivoxyl

1403836-41-8

adefovir dipivoxil:nicotinamide cocrystal

Conditions
ConditionsYield
In ethyl acetate at 20 - 70℃; for 25.25h; Product distribution / selectivity;80%
142340-99-6

adefovir dipivoxyl

65-45-2

salicylamide

adefovir dipivoxil:salicylamide cocrystal

Conditions
ConditionsYield
In tert-butyl methyl ether; acetone at 20℃; Product distribution / selectivity; Reflux;78%
3282-30-2

pivaloyl chloride

142340-99-6

adefovir dipivoxyl

bis[(2-(6-pivaloylamino-9H-purin-9-yl)ethoxy)methyl]phosphonic acid bis(pivaloyloxymethyl) ester

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 8h; Cooling with ice;76.13%
142340-99-6

adefovir dipivoxyl

1443213-13-5

9-{2-[O,O'-bis(pivaloyloxymethyl)thiophosphonomethoxy]ethyl}adenine

Conditions
ConditionsYield
With 2,4-bis(methylthio)-1,3-dithia-2,4-diphosphetane-2,4-disulfide In benzene at 0 - 80℃; for 2.5h;29%
142340-99-6

adefovir dipivoxyl

1110441-05-8

adefovir dipivoxil monohydrate

Conditions
ConditionsYield
With water In dichloromethane at 20 - 25℃; for 24h;
With water for 24h;
64-18-6

formic acid

142340-99-6

adefovir dipivoxyl

adefovir dipivoxil formic acid

Conditions
ConditionsYield
In ethyl acetate at 20 - 40℃;
142340-99-6

adefovir dipivoxyl

106941-25-7

Adefovir

Conditions
ConditionsYield
With ethylenediaminetetraacetic acid; DL-dithiothreitol; water; magnesium chloride In aq. buffer at 37℃; for 1h; pH=7.5; Enzymatic reaction;
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    Adefovir dipivoxil

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    Adefovir Dipivoxyl CAS:142340-99-6

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    Chemical Name: Adefovir dipivoxil Molecular Formula: C20H32N5O8P Formula Weight: 501.47 CAS No.: 142340-99-6 EINECS:200-001-8 White to white crystalline powder. Adefovir Dipivoxyl is a prescription medicine used to treat infections

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    Product Name: Adefovir dipivoxil Synonyms: BIS POM PMEA;BIS(PIVALOYLOXYMETHYL)-9-[2-(PHOSPHONOMETHOXY)ETHYL]ADENINE;9-[2-[bis[(pivaloyloxy)methoxy]phosphinyl]methoxy]ethyl]adenine;ADEFOVIR DIPIVOXIL;ADEFOVI

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Chemistry

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

Production

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 Profile

Safety Information of Adefovir dipivoxil (CAS NO. 142340-99-6):
Hazard Codes: Xn Harmful
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

Specification

  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 .