methyl 2-(2-{[(benzyloxy)carbonyl]amino}propan-2-yl)-5-hydroxy-6-oxo-1,6-dihydropyrimidine-4-carboxylate

• ChemBase ID: 167655
• Molecular Formular: C17H19N3O6
• Molecular Mass: 361.34926
• Monoisotopic Mass: 361.12738534
• SMILES: [nH]1c(nc(c(c1=O)O)C(=O)OC)C(NC(=O)OCc1ccccc1)(C)C
• Canonical SMILES: COC(=O)c1nc([nH]c(=O)c1O)C(NC(=O)OCc1ccccc1)(C)C
• InChI: InChI=1S/C17H19N3O6/c1-17(2,20-16(24)26-9-10-7-5-4-6-8-10)15-18-11(14(23)25-3)12(21)13(22)19-15/h4-8,21H,9H2,1-3H3,(H,20,24)(H,18,19,22)
• InChIKey: NIVUTAZNLHLBAN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl 2-(2-{[(benzyloxy)carbonyl]amino}propan-2-yl)-5-hydroxy-6-oxo-1,6-dihydropyrimidine-4-carboxylate
• IUPAC Traditional name: methyl 2-(2-{[(benzyloxy)carbonyl]amino}propan-2-yl)-5-hydroxy-6-oxo-1H-pyrimidine-4-carboxylate
• Synonyms: Methyl 2-(2-(benzyloxycarbonylamino)propan-2-yl)-5-hydroxy-6-oxo-1,6-dihydropyrimidine-4-carboxylate; 1,6-Dihydro-5-hydroxy-2-[1-methyl-1-[[benzylcarbamoyl]amino]ethyl]-6-oxo-4-pyrimidinecarboxylic Acid Methyl Ester; Methyl2-(2-(benzyloxycarbonylaMino)propan-2-yl)-5-hydroxy-6-oxo-1,6-dihydropyriMidine-4-carboxylate

Database IDs

• CAS Number: 519032-08-7
• MDL Number: MFCD12026362
• PubChem SID: 162261788
• PubChem CID: 54683039

CALCULATED PROPERTIES

• Acid pKa: 5.5697722
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 1.2239659
• LogD (pH = 7.4): -0.31021655
• Log P: 1.4909568
• Molar Refractivity: 91.6384 cm^3
• Polarizability: 34.95623 Å^3
• Polar Surface Area: 126.32 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; DMSO
• Apperance: Brown Solid

Product Information

• Purity: 95+%; 97%

DETAILS

Toronto Research Chemicals - D449235

An intermediate in the preparation of HIV-integrase inhibitors

REFERENCES

• Summa, V., et al.: J. Med. Chem., 51, 5843 (2008)