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

• ChemBase ID: 160307
• Molecular Formular: C14H17N3O4
• Molecular Mass: 291.30248
• Monoisotopic Mass: 291.12190604
• SMILES: c1c(ccc(c1)N1C(=O)COCC1)N1C(=O)O[C@H](C1)CN
• Canonical SMILES: NC[C@@H]1OC(=O)N(C1)c1ccc(cc1)N1CCOCC1=O
• InChI: InChI=1S/C14H17N3O4/c15-7-12-8-17(14(19)21-12)11-3-1-10(2-4-11)16-5-6-20-9-13(16)18/h1-4,12H,5-9,15H2/t12-/m0/s1
• InChIKey: DEXXSYVEWAYIGZ-LBPRGKRZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one
• IUPAC Traditional name: 4-{4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one
• Synonyms: Des(5-chloro-2-carboxythienyl) Rivaroxaban; 4-[4-[(5S)-5-(Aminomethyl)-2-oxo-3-oxazolidinyl]phenyl]-3-morpholinone; (S)-4-(4-(5-(Aminomethyl)-2-oxooxazolidin-3-yl)phenyl)morpholin-3-one

Database IDs

• CAS Number: 446292-10-0
• MDL Number: MFCD11977666
• PubChem SID: 162254442
• PubChem CID: 11346837

CALCULATED PROPERTIES

• Acid pKa: 15.858414
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): -3.410433
• LogD (pH = 7.4): -2.2598572
• Log P: -0.45829836
• Molar Refractivity: 73.7748 cm^3
• Polarizability: 28.967562 Å^3
• Polar Surface Area: 85.1 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Solid

Product Information

• Purity: 95+%

DETAILS

Toronto Research Chemicals - A616975

Rivaroxaban intermediate.

REFERENCES

• Roehrig, S., et al.: J. Med. Chem., 48, 5900 (2005)
• Weinz, C., et al.: Drug Metab. Disposition, 37, 1056 (2005)