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

• ChemBase ID: 165457
• Molecular Formular: C14H18FN3O3
• Molecular Mass: 295.3094232
• Monoisotopic Mass: 295.13321967
• SMILES: O1CCN(CC1)c1c(cc(cc1)N1C[C@@H](OC1=O)CN)F
• Canonical SMILES: NC[C@@H]1OC(=O)N(C1)c1ccc(c(c1)F)N1CCOCC1
• InChI: InChI=1S/C14H18FN3O3/c15-12-7-10(18-9-11(8-16)21-14(18)19)1-2-13(12)17-3-5-20-6-4-17/h1-2,7,11H,3-6,8-9,16H2/t11-/m0/s1
• InChIKey: VXIWZOWWQMRVRF-NSHDSACASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5S)-5-(aminomethyl)-3-[3-fluoro-4-(morpholin-4-yl)phenyl]-1,3-oxazolidin-2-one
• IUPAC Traditional name: (5S)-5-(aminomethyl)-3-[3-fluoro-4-(morpholin-4-yl)phenyl]-1,3-oxazolidin-2-one
• Synonyms: (5S)-5-(Aminomethyl)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxazolidinone; (-)-(S)-5-(Aminomethyl)-3-(3-fluoro-4-morpholinophenyl)oxazolidin-2-one; (S)-N-[[3-[3-Fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]amine; PNU 105868; Deacetyl Linezolid

Database IDs

• CAS Number: 168828-90-8
• PubChem SID: 162259590
• PubChem CID: 10780199

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): -2.066412
• LogD (pH = 7.4): -0.70283145
• Log P: 0.81781703
• Molar Refractivity: 75.031 cm^3
• Polarizability: 28.603527 Å^3
• Polar Surface Area: 68.03 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Methanol
• Apperance: Off-white Solid
• Melting Point: 84-89°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D198960

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)