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Tenofovir disoproxil fumarate
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Name

Tenofovir disoproxil fumarate

 EINECS 687-766-5
CAS No. 202138-50-9 Density 1.45 g/cm3
PSA 269.85000 LogP 3.32860
Solubility N/A Melting Point 219oC
Formula C19H30N5O10P.C4H4O4 Boiling Point 642.7 °C at 760 mmHg
Molecular Weight 635.522 Flash Point 342.5 °C
Transport Information N/A Appearance almost white crystalline
Safety 26-36 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 202138-50-9 (Tenofovir disoproxil fumarate) Hazard Symbols IrritantXi
Synonyms

TDF;PMPA prodrug;Tenofovir Disoproxil Fumarate [USAN];9-((R)-2-((Bis(((isopropoxycarbonyl)oxy)methoxy)phosphinyl)methoxy)propyl)adenine, fumarate;201341-05-1;Bis(NeopentylOC)PMPA;Viread;GS 4331-05 (*1:1 Fumarate salt*);Viread (*1:1 Fumarate salt*);Truvada;Tenofovir DF;[[(2R)-1-(6-aminopurin-9-yl)propan-2-yl]oxymethyl-(propan-2-yloxycarbonyloxymethoxy)phosphoryl]oxymethyl propan-2-yl carbonate;

Article Data 42

Tenofovir disoproxil fumarate Synthetic route

110-17-8

(2E)-but-2-enedioic acid

tenofovir disoproxil

202138-50-9

tenofovir disoproxyl fumarate

Conditions
ConditionsYield
In isopropyl alcohol at 50 - 55℃;94.4%
In isopropyl alcohol at 50 - 55℃; for 1h;92.2%
In methanol; water at 0 - 75℃; for 0.5h; Solvent; Temperature;90%
35180-01-9

chloromethyl isopropyl carbonate

110-17-8

(2E)-but-2-enedioic acid

147127-20-6

tenofovir

202138-50-9

tenofovir disoproxyl fumarate

Conditions
ConditionsYield
Stage #1: tenofovir With triethylamine In 1-methyl-pyrrolidin-2-one at 63℃; for 0.5h;
Stage #2: chloromethyl isopropyl carbonate In 1-methyl-pyrrolidin-2-one at 63℃; for 4h;
Stage #3: (2E)-but-2-enedioic acid In isopropyl alcohol at 50℃; for 0.5h; Concentration;		90%
Stage #1: chloromethyl isopropyl carbonate; tenofovir With tetrabutylammomium bromide; triethylamine at 50℃; for 3h; Inert atmosphere;
Stage #2: (2E)-but-2-enedioic acid In isopropyl alcohol Reagent/catalyst; Temperature; Reflux;		78.8%
Stage #1: chloromethyl isopropyl carbonate; tenofovir With tetrabutylammomium bromide; triethylamine In 1-methyl-pyrrolidin-2-one; toluene at 45 - 55℃; for 5h;
Stage #2: (2E)-but-2-enedioic acid In isopropyl alcohol at 50 - 55℃; for 2h;		63.6%

9-[2-[(R)[[bis[[isopropoxycarbonyl]oxy]methoxy]phosphinyl]methoxy]propyl]adenine orotate

110-17-8

(2E)-but-2-enedioic acid

202138-50-9

tenofovir disoproxyl fumarate

Conditions
ConditionsYield
Stage #1: 9-[2-[(R)[[bis[[isopropoxycarbonyl]oxy]methoxy]phosphinyl]methoxy]propyl]adenine orotate With triethylamine In dichloromethane; water at 25℃;
Stage #2: (2E)-but-2-enedioic acid In isopropyl alcohol at 0 - 50℃;		83%
66224-66-6, 66224-67-7, 66224-68-8, 66224-69-9, 134434-48-3, 134434-49-4, 134454-76-5, 134461-75-9

adenine

202138-50-9

tenofovir disoproxyl fumarate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: sodium hydroxide / N,N-dimethyl-formamide / 120 °C
2.1: magnesium 2-methylpropan-2-olate / 1-methyl-pyrrolidin-2-one / 70 - 74 °C
3.1: chloro-trimethyl-silane; sodium bromide / 1-methyl-pyrrolidin-2-one / 0 - 75 °C
4.1: triethylamine / 1-methyl-pyrrolidin-2-one / 45 °C
4.2: 5.5 h / 45 - 50 °C
5.1: isopropyl alcohol / 2 h / 50 °C
View Scheme
Multi-step reaction with 5 steps
1.1: potassium carbonate / N,N-dimethyl-formamide / 100 - 120 °C / Inert atmosphere
1.2: 8 h / 120 °C
2.1: magnesium 2-methylpropan-2-olate / N,N-dimethyl-formamide; water / 44 h / -15 - 20 °C / Inert atmosphere
3.1: hydrogenchloride / water / 0.5 h / 140 °C / Microwave irradiation
4.1: triethylamine / 1-methyl-pyrrolidin-2-one / 1 h / 45 °C / Inert atmosphere
4.2: 5 h / 60 °C
5.1: cyclohexane / 0.17 h / 60 °C
View Scheme
Multi-step reaction with 5 steps
1.1: sodium carbonate / N,N-dimethyl-formamide / 6 h / 95 °C
2.1: lithium tert-butoxide / N,N-dimethyl-formamide / 2 h / 0 - 20 °C
2.2: 0 °C
3.1: hydrogen bromide / 8 h / 80 °C
4.1: triethylamine; benzyltriethylammonium bromide / N,N-dimethyl-formamide / 4 h / 60 °C
5.1: isopropyl alcohol / 2.5 h / 60 °C
View Scheme
Multi-step reaction with 4 steps
1.1: sodium hydroxide / N,N-dimethyl-formamide / 0.33 h / 20 °C
1.2: 24.5 h / 120 °C
2.1: lithium tert-butoxide / N,N-dimethyl-formamide / 30 - 35 °C
3.1: trimethylsilyl bromide / acetonitrile / 5 h / Reflux
4.1: triethylamine; tetrabutylammomium bromide / 1-methyl-pyrrolidin-2-one; toluene / 5 h / 45 - 55 °C
4.2: 2 h / 50 - 55 °C
View Scheme
Multi-step reaction with 4 steps
1.1: sodium hydroxide / N,N-dimethyl-formamide / 0.33 h / 20 °C
1.2: 24.5 h / 120 °C
2.1: magnesium 2-methylpropan-2-olate; calcium hydride / N,N-dimethyl-formamide / 30 - 35 °C
3.1: trimethylsilyl bromide / acetonitrile / 5 h / Reflux
4.1: toluene; 1-methyl-pyrrolidin-2-one / 60 °C
4.2: 5 h / 45 - 55 °C
4.3: 2 h / 50 - 55 °C
View Scheme
14047-28-0

(R)-9-(2-hydroxypropyl)adenine

202138-50-9

tenofovir disoproxyl fumarate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: magnesium 2-methylpropan-2-olate / 1-methyl-pyrrolidin-2-one / 70 - 74 °C
2.1: chloro-trimethyl-silane; sodium bromide / 1-methyl-pyrrolidin-2-one / 0 - 75 °C
3.1: triethylamine / 1-methyl-pyrrolidin-2-one / 45 °C
3.2: 5.5 h / 45 - 50 °C
4.1: isopropyl alcohol / 2 h / 50 °C
View Scheme
Multi-step reaction with 4 steps
1.1: magnesium 2-methylpropan-2-olate / toluene; 1-methyl-pyrrolidin-2-one / 6 h / 25 - 75 °C
1.2: 1 h
1.3: 90 - 95 °C
2.1: toluene / 20 - 110 °C
3.1: chloro-trimethyl-silane; triethylamine; tetrabutylammomium bromide / 1-Methylpyrrolidine / 50 - 55 °C
3.2: 5 h / 50 - 55 °C
4.1: isopropyl alcohol / 50 °C
View Scheme
Multi-step reaction with 4 steps
1.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 - 35 °C
1.2: 2 h / 25 - 30 °C
1.3: 5 h / 25 - 75 °C
2.1: hydrogen bromide / water / 5 h / 90 - 95 °C
2.2: 4 h / 0 - 30 °C / pH 2.5 - 3
3.1: triethylamine / cyclohexane / 2 h / 80 - 85 °C
3.2: 4 h / 50 - 55 °C
4.1: isopropyl alcohol / 0.33 h / 50 - 55 °C
4.2: 5.5 h / 0 - 55 °C
View Scheme
147127-20-6

tenofovir

202138-50-9

tenofovir disoproxyl fumarate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: triethylamine / 1-methyl-pyrrolidin-2-one / 45 °C
1.2: 5.5 h / 45 - 50 °C
2.1: isopropyl alcohol / 2 h / 50 °C
View Scheme
Multi-step reaction with 3 steps
1.1: toluene / 20 - 110 °C
2.1: chloro-trimethyl-silane; triethylamine; tetrabutylammomium bromide / 1-Methylpyrrolidine / 50 - 55 °C
2.2: 5 h / 50 - 55 °C
3.1: isopropyl alcohol / 50 °C
View Scheme
Multi-step reaction with 2 steps
1.1: triethylamine / 1-methyl-pyrrolidin-2-one / 1 h / 45 °C / Inert atmosphere
1.2: 5 h / 60 °C
2.1: cyclohexane / 0.17 h / 60 °C
View Scheme
180587-75-1

(R)-diethyl (((1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)phosphonate

202138-50-9

tenofovir disoproxyl fumarate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: chloro-trimethyl-silane; sodium bromide / 1-methyl-pyrrolidin-2-one / 0 - 75 °C
2.1: triethylamine / 1-methyl-pyrrolidin-2-one / 45 °C
2.2: 5.5 h / 45 - 50 °C
3.1: isopropyl alcohol / 2 h / 50 °C
View Scheme
Multi-step reaction with 3 steps
1.1: hydrogen bromide / water / 5 h / 90 - 95 °C
1.2: 4 h / 0 - 30 °C / pH 2.5 - 3
2.1: triethylamine / cyclohexane / 2 h / 80 - 85 °C
2.2: 4 h / 50 - 55 °C
3.1: isopropyl alcohol / 0.33 h / 50 - 55 °C
3.2: 5.5 h / 0 - 55 °C
View Scheme
Multi-step reaction with 3 steps
1.1: hydrogen bromide / water / 2 h / 90 - 95 °C
1.2: 5 h / 0 - 30 °C / pH 2.5
2.1: triethylamine / cyclohexane / 2 h / 20 - 85 °C
2.2: 4 h / 25 - 55 °C
2.3: pH 6.5 - 7.5
3.1: isopropyl alcohol / 0.33 h / 50 - 55 °C
3.2: 5.5 h / 0 - 55 °C
View Scheme
1215085-38-3

tenofovir disoproxil chloromethyl-isopropyl carbonate

110-17-8

(2E)-but-2-enedioic acid

202138-50-9

tenofovir disoproxyl fumarate

Conditions
ConditionsYield
In isopropyl alcohol at 50℃;
35180-01-9

chloromethyl isopropyl carbonate

(x)C6H15N*C9H14N5O4P

202138-50-9

tenofovir disoproxyl fumarate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: chloro-trimethyl-silane; triethylamine; tetrabutylammomium bromide / 1-Methylpyrrolidine / 50 - 55 °C
1.2: 5 h / 50 - 55 °C
2.1: isopropyl alcohol / 50 °C
View Scheme
160616-04-6

bis(2-propyl) (R)-9-(2-phosphonomethoxypropyl)adenine

202138-50-9

tenofovir disoproxyl fumarate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: hydrogenchloride / water / 0.5 h / 140 °C / Microwave irradiation
2.1: triethylamine / 1-methyl-pyrrolidin-2-one / 1 h / 45 °C / Inert atmosphere
2.2: 5 h / 60 °C
3.1: cyclohexane / 0.17 h / 60 °C
View Scheme

Tenofovir disoproxil fumarate Specification

The Tenofovir disoproxil fumarate with the cas number 202138-50-9, is also called (1)(R)-5-((2-(6-Amino-9H-purin-9-yl)-1-methylethoxy)methyl)-2,4,6,8-tetraoxa-5-phosphanonanedioic acid, bis(1-methylethyl) ester, 5-oxide, (E)-2-butenedioate (1:1); (2)9-((R)-2-((Bis(((isopropoxycarbonyl)oxy)methoxy)phosphinyl)methoxy)propyl)adenine fumarate (1:1); (3)Bis(hydroxymethyl) (((R)-2-(6-amino-9H-purin-9-yl)-1-methylethoxy)methyl)phosphonate, bis(isopropyl carbonate)(ester), fumarate (1:1); (4) PMPA prodrug; (5) TDF; (6) Tenofovir DF; (7) Tenofovir disoproxil fumarate; (8) UNII-OTT9J7900I; (9) Viread.

The Tenofovir disoproxil fumarate has a brand name VIREAD. It is obtained from a fumaric acid salt of bis-isopropoxycarbonyloxymethyl ester derivative of tenofovir. Tenofovir disoproxil fumarate is converted to tenofovir, which is an acyclic nucleoside phosphonate (nucleotide) analog of adenosine 5'-monophosphate. Tenofovir exhibits activity against HIV-1 reverse transcriptase. VIREAD are taken orally . The most common aderse reactions include: light to moderate gastrointestinal upset (diarrhea, nausea, vomiting, and flatulence), Metabolic system of low incidence (1%) disease phosphatase, serum phosphate light to moderate decrease. It can also show dangerous lactic acidosis.

Physical properties of Tenofovir disoproxil fumarate are: (1)ACD/LogP: 2.037; (2)# of Rule of 5 Violations: 2; (3)ACD/LogD (pH 5.5): 2.01; (4)ACD/LogD (pH 7.4): 2.04; (5)ACD/BCF (pH 5.5): 19.53; (6)ACD/BCF (pH 7.4): 20.78; (7)ACD/KOC (pH 5.5): 286.95; (8)ACD/KOC (pH 7.4): 305.32; (9)#H bond acceptors: 15; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 17; (12)Flash Point: 342.5 °C; (13)Enthalpy of Vaporization: 94.85 kJ/mol; (14)Boiling Point: 642.7 °C at 760 mmHg; (15)Vapour Pressure: 2.06E-16 mmHg at 25°C

You can still convert the following datas into molecular structure :
1. O=C(O)\C=C\C(=O)O.O=P(OCOC(=O)OC(C)C)(OCOC(=O)OC(C)C)CO[C@H](C)Cn1c2ncnc(c2nc1)N
2. InChI=1/C19H30N5O10P.C4H4O4/c1-12(2)33-18(25)28-9-31-35(27,32-10-29-19(26)34-13(3)4)11-30-14(5)6-24-8-23-15-16(20)21-7-22-17(15)24;5-3(6)1-2-4(7)8/h7-8,12-14H,6,9-11H2,1-5H3,(H2,20,21,22);1-2H,(H,5,6)(H,7,8)/b;2-1+/t14-;/m1./s1

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