(5R)-5-(azidomethyl)-3-[3-fluoro-4-(morpholin-4-yl)phenyl]-1,3-oxazolidin-2-one

• ChemBase ID: 165431
• Molecular Formular: C14H16FN5O3
• Molecular Mass: 321.3069432
• Monoisotopic Mass: 321.12371762
• SMILES: O1CCN(CC1)c1c(cc(cc1)N1C[C@@H](OC1=O)CN=[N+]=[N-])F
• Canonical SMILES: [N-]=[N+]=NC[C@@H]1OC(=O)N(C1)c1ccc(c(c1)F)N1CCOCC1
• InChI: InChI=1S/C14H16FN5O3/c15-12-7-10(1-2-13(12)19-3-5-22-6-4-19)20-9-11(8-17-18-16)23-14(20)21/h1-2,7,11H,3-6,8-9H2/t11-/m0/s1
• InChIKey: FQUBFDDPWLBKIZ-NSHDSACASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5R)-5-(azidomethyl)-3-[3-fluoro-4-(morpholin-4-yl)phenyl]-1,3-oxazolidin-2-one
• IUPAC Traditional name: (5R)-5-(azidomethyl)-3-[3-fluoro-4-(morpholin-4-yl)phenyl]-1,3-oxazolidin-2-one
• Synonyms: (5R)-5-(Azidomethyl)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxazolidinone; (R)-5-(Azidomethyl)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxazolidinone; Deacetamide Linezolid Azide

Database IDs

• CAS Number: 168828-84-0
• PubChem SID: 162259564
• PubChem CID: 10519785

CALCULATED PROPERTIES

• Acid pKa: 19.802187
• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): 1.6309975
• LogD (pH = 7.4): 1.6309977
• Log P: 1.7450433
• Molar Refractivity: 79.666 cm^3
• Polarizability: 29.441753 Å^3
• Polar Surface Area: 71.44 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D195600

An impurity of Linezolid (L466500), as antimycobacterial agent.

REFERENCES

• Sato, K., et al.: Eur. J. Pharmacol., 347, 231 (1998)
• Maignan, S., et al.: J. Med. Chem., 43, 3226 (1998)
• Tokuyama, R., et al.: Chem. Pharm. Bull., 49, 353 (1998)