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764659-72-5

Basic Information
CAS No.: 764659-72-5
Name: (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl)-1,3-Oxathiolane-2-carboxylic acid, (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester
Article Data: 14
Molecular Structure:
Molecular Structure of 764659-72-5 ((2R,5S)-5-(4-amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl)-1,3-Oxathiolane-2-carboxylic acid, (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester)
Formula: C18H26FN3O4S
Molecular Weight: 399.487
Synonyms: (2R,5S)-5-(4-Amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl)-1,3-oxathiolane-2-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester; emtricitabine intermediate FCME
EINECS: 1592732-453-0
Density: 1.47
Boiling Point: 508.5±60.0 °C(Predicted)
PSA: 122.73000
LogP: 2.89910
Synthetic route

C21H31FN4O4S

764659-72-5

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carboxylate

Conditions
ConditionsYield
With hydrogenchloride In dichloromethane; water at 20 - 25℃;96.7%
2022-85-7

Flucytosine

147027-09-6

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5R)-5-(methylcarbonyloxy)-1,3-oxathiolane-2-carboxylate

764659-72-5

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carboxylate

Conditions
ConditionsYield
Stage #1: (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5R)-5-(methylcarbonyloxy)-1,3-oxathiolane-2-carboxylate With triethylsilane; iodine In dichloromethane at 0℃; for 1h; Inert atmosphere;
Stage #2: Flucytosine With N,O-bis-(trimethylsilyl)-acetamide In dichloromethane at 0 - 20℃; for 1h; Reagent/catalyst; Inert atmosphere; stereoselective reaction;
91%
Stage #1: Flucytosine With chloro-trimethyl-silane; 1,1,1,3,3,3-hexamethyl-disilazane at 25 - 130℃; Inert atmosphere;
Stage #2: (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5R)-5-(methylcarbonyloxy)-1,3-oxathiolane-2-carboxylate With zirconium(IV) chloride In dichloromethane at 25 - 30℃; for 6h; Inert atmosphere;
80%
111878-21-8

2-trimethylsilyloxy-4-trimethylsilylamino-5-fluoropyrimidine

288325-76-8

5S-chloro-[1,3]oxathiolane-2R-carboxilic acid 2-(1'R,2'S,5'R)-isopropyl-5-methyl-cyclohexyl ester

764659-72-5

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carboxylate

Conditions
ConditionsYield
Stage #1: 2-trimethylsilyloxy-4-trimethylsilylamino-5-fluoropyrimidine; 5S-chloro-[1,3]oxathiolane-2R-carboxilic acid 2-(1'R,2'S,5'R)-isopropyl-5-methyl-cyclohexyl ester With triethylamine In dichloromethane at 42 - 45℃; for 19h; Heating / reflux;
Stage #2: With water at 25℃; for 0.5h;
81%
2022-85-7

Flucytosine

5R-hydroxy-[1,3]oxathiolane-2R-carboxylic acid 2-(1'R,2'S,5'R)-isopropyl-5-methyl-cyclohexyl ester

764659-72-5

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carboxylate

Conditions
ConditionsYield
Stage #1: 5R-hydroxy-[1,3]oxathiolane-2R-carboxylic acid 2-(1'R,2'S,5'R)-isopropyl-5-methyl-cyclohexyl ester With thionyl chloride In dichloromethane at 0 - 15℃; for 2h;
Stage #2: Flucytosine With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane In toluene Reflux;
Stage #3: With triethylamine at 90℃; Reflux;
50.5%
Stage #1: 5R-hydroxy-[1,3]oxathiolane-2R-carboxylic acid 2-(1'R,2'S,5'R)-isopropyl-5-methyl-cyclohexyl ester With thionyl chloride In dichloromethane; toluene; N,N-dimethyl-d6-formamide at 10 - 15℃; for 2h;
Stage #2: Flucytosine With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane In dichloromethane; N,N-dimethyl-formamide; toluene Reflux; Further stages;
50.5%

5-chloro-[1,3]oxathiolane-2-carboxylic acid 2-isopropyl-5-methyl-cyclohexyl ester

764659-72-5

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carboxylate

Conditions
ConditionsYield
Stage #1: Flucytosine With methanesulfonic acid; 1,1,1,3,3,3-hexamethyl-disilazane In toluene for 3h;
Stage #2: 5-chloro-[1,3]oxathiolane-2-carboxylic acid 2-isopropyl-5-methyl-cyclohexyl ester With triethylamine In dichloromethane at 20 - 25℃; for 20 - 21h; Heating / reflux;
Multi-step reaction with 4 steps
1.1: triethylamine / dichloromethane / 8 - 50 °C
2.1: toluene / 1 h / Molecular sieve
3.1: toluene / 75 - 80 °C
4.1: methanesulfonic acid / methanol / 4 h
4.2: 0.17 h
View Scheme
147126-65-6

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(methylcarbonyloxy)-1,3-oxathiolane-2-carboxylate

764659-72-5

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carboxylate

Conditions
ConditionsYield
Stage #1: Flucytosine With methanesulfonic acid; 1,1,1,3,3,3-hexamethyl-disilazane In toluene for 3h; Heating / reflux;
Stage #2: (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(methylcarbonyloxy)-1,3-oxathiolane-2-carboxylate With trimethylsilyl iodide In dichloromethane at 20℃; for 2h;
2022-85-7

Flucytosine

(2R,5R)-5-hydroxy-[1,3]-oxathiolane-2-carboxylic acid, 2S-isopropyl-5R-methyl-1R-cyclohexyl ester

764659-72-5

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carboxylate

Conditions
ConditionsYield
Stage #1: (2R,5R)-5-hydroxy-[1,3]-oxathiolane-2-carboxylic acid, 2S-isopropyl-5R-methyl-1R-cyclohexyl ester With thionyl chloride; methanesulfonic acid; N,N-dimethyl-formamide In dichloromethane at 8 - 20℃; for 8h; Heating / reflux;
Stage #2: Flucytosine With 1,1,1,3,3,3-hexamethyl-disilazane In dichloromethane; toluene for 5h; Heating / reflux;
Stage #3: With triethylamine In dichloromethane; water; toluene at 25 - 65℃; for 6h; pH=7.8; Heating / reflux;
147126-62-3

(2R,5R)-5-hydroxy-1,3-oxathiolane-2-carboxylic acid (1R,2S,5R)-5-methyl-2-isopropylcyclohexyl ester

764659-72-5

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: pyridine / dmap / di-isopropyl ether / 5 - 20 °C
2.1: 1,1,1,3,3,3-hexamethyl-disilazane / methanesulfonic acid / toluene / 6 h / Reflux
2.2: 10 - 55 °C
3.1: methanesulfonic acid / di-isopropyl ether; methanol / 0.83 h / 20 °C
3.2: 1 h / 20 °C
View Scheme
1144099-18-2

(1'R,2'S,5'R)-menthyl-5(R,S)-acetoxy-[1,3]-oxathiolane-2R-carboxylate

764659-72-5

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 1,1,1,3,3,3-hexamethyl-disilazane / methanesulfonic acid / toluene / 6 h / Reflux
1.2: 10 - 55 °C
2.1: methanesulfonic acid / di-isopropyl ether; methanol / 0.83 h / 20 °C
2.2: 1 h / 20 °C
View Scheme

C21H30FN3O5S

764659-72-5

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carboxylate

Conditions
ConditionsYield
Stage #1: C21H30FN3O5S With methanesulfonic acid In methanol; di-isopropyl ether at 20℃; for 0.833333h;
Stage #2: With triethylamine In hexane; water; ethyl acetate at 20℃; for 1h;
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