(2R-cis)-5-(4-aMino-2-oxo-1(2H)-pyriMidinyl)-1,3-oxathiolane-2-carboxylic Acid Chemical Properties

Melting point:

>208°C (dec.)

Boiling point:

546.6±60.0 °C(Predicted)

Density 

1.87±0.1 g/cm3(Predicted)

storage temp. 

Hygroscopic, Refrigerator, Under Inert Atmosphere

solubility 

Dimethylformamide; Methanol

pka

1.94±0.40(Predicted)

form 

Solid

color 

White to Off-White

Stability:

Hygroscopic

Major Application

pharmaceutical

InChI

1S/C8H9N3O4S/c9-4-1-2-11(8(14)10-4)5-3-16-7(15-5)6(12)13/h1-2,5,7H,3H2,(H,12,13)(H2,9,10,14)/t5-,7+/m0/s1

InChIKey

PIIRVEZNDVLYQA-CAHLUQPWSA-N

SMILES

S1[C@@H](O[C@@H](C1)[n]2[c](nc(cc2)N)=O)C(=O)O

CAS DataBase Reference

173829-09-9

Safety Information

WGK Germany 

WGK 3

Storage Class

11 - Combustible Solids

(2R-cis)-5-(4-aMino-2-oxo-1(2H)-pyriMidinyl)-1,3-oxathiolane-2-carboxylic Acid Usage And Synthesis

Uses

Lamivudine Acid (Lamivudine EP Impurity A) is an impurity of Lamivudine (L172500). Impurity A per European Pharmacopoeia.

Synthesis

Preparation of lamivudine impurity A lamivudine acid: 100 ml of methanol-water solution (1:1) was added to a 250 ml round-bottomed flask, 50 ml of 25% aqueous sodium hydroxide solution was added, and 5S-cytosine-1’- 1,3-oxathiolane-2-carboxylic acid-(1’R,2’S,5’R) menthyl ester (CME) 20g, stirred at 25??. The reaction was carried out for 5 h. When the solution was clarified, the reaction was stopped, the organic phase was removed by extraction with dichloromethane, the aqueous phase was collected, the pH was adjusted to 3-4 with dilute hydrochloric acid solution under stirring at 0-5??C, and after stirring for about 20 min, a pale white solid was precipitated, filtered, washed with water, dried and recrystallized to obtain the white crystalline powder lamivudine impurity A, i.e.: (2R-cis)-5-(4-aMino-2-oxo-1(2H)-pyriMidinyl)-1,3-oxathiolane-2-carboxylic Acid (abbreviation: lamivudine acid), HPLC purity >98%.

(2R-cis)-5-(4-aMino-2-oxo-1(2H)-pyriMidinyl)-1,3-oxathiolane-2-carboxylic Acid(173829-09-9)Related Product Information

• 3-Chloro TirofiBan
• 2-hydroxy-5-((4-oxo-3,4-dihydrophthalazin-1-yl)methyl)benzonitrile
• N-(2,6-dimethylphenyl)-2-((2,6-dimethylphenyl)amino)acetamide
• 1,2-Cyclopentanediol, 3-[7-aMino-5-(propylthio)-3H-1,2,3-triazolo[4,5-d]pyriMidin-3-yl]-5-(2-hydroxyethoxy)-, (1S,2S,3R,5S)-
• Tirofiban hydrochloride Impurity 6
• Olaparib impurity 1
• 3-((4-Oxo-3,4-dihydrophthalazin-1-yl)methyl)benzoic acid
• Ticagrelor Sulfone
• lignocaine N-oxide
• 4-amino-1-((2R,3R,5S)-2-(hydroxymethyl)-3-oxido-1,3-oxathiolan-5-yl)pyrimidin-2(1H)-one
• 5'-Epi-LaMivudine
• lamivudine sulfoxide
• Aids004768
• Lamivudine
• Lamivudine Impurity 1
• ent-LaMivudine
• Cytosine
• Salicylic acid