2-{[(5S)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl]methyl}-2,3-dihydro-1H-isoindole-1,3-dione

• ChemBase ID: 176701
• Molecular Formular: C22H19N3O6
• Molecular Mass: 421.40276
• Monoisotopic Mass: 421.12738534
• SMILES: c1c(ccc(c1)N1C(=O)COCC1)N1C(=O)O[C@H](C1)CN1C(=O)c2c(C1=O)cccc2
• Canonical SMILES: O=C1O[C@H](CN1c1ccc(cc1)N1CCOCC1=O)CN1C(=O)c2c(C1=O)cccc2
• InChI: InChI=1S/C22H19N3O6/c26-19-13-30-10-9-23(19)14-5-7-15(8-6-14)24-11-16(31-22(24)29)12-25-20(27)17-3-1-2-4-18(17)21(25)28/h1-8,16H,9-13H2/t16-/m1/s1
• InChIKey: KUQNYAUTIWQAKY-MRXNPFEDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{[(5S)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl]methyl}-2,3-dihydro-1H-isoindole-1,3-dione
• IUPAC Traditional name: 2-{[(5S)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl]methyl}isoindole-1,3-dione
• Synonyms: 2-[[(5S)-2-Oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-5-oxazolidinyl]methyl]-1H-isoindole-1,3(2H)-dione; 4-[4-[(5S)-5-Phthalimidomethyl-2-oxo-3-oxazolidinyl]phenyl]-3-morpholinone; (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione

Database IDs

• CAS Number: 446292-08-6
• MDL Number: MFCD11977665
• PubChem SID: 164232611
• PubChem CID: 11690317

CALCULATED PROPERTIES

• Acid pKa: 15.858414
• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): 1.0842596
• LogD (pH = 7.4): 1.0842596
• Log P: 1.0842596
• Molar Refractivity: 108.0675 cm^3
• Polarizability: 40.888332 Å^3
• Polar Surface Area: 96.46 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Solid

Product Information

• Purity: 95+%

DETAILS

Toronto Research Chemicals - P385850

Rivaroxaban intermediate.

REFERENCES

• Roehrig, S., et al.: J. Med. Chem., 48, 5900 (2005)