2-(morpholin-4-yl)ethyl (4E)-6-{4-hydroxy-6-methoxy-7-methyl-1-[2-(morpholin-4-yl)ethoxy]-3-oxo-1,3-dihydro-2-benzofuran-5-yl}-4-methylhex-4-enoate

• ChemBase ID: 174828
• Molecular Formular: C29H42N2O9
• Molecular Mass: 562.65178
• Monoisotopic Mass: 562.28903093
• SMILES: c1(c(c(c2c(c1O)C(=O)OC2OCCN1CCOCC1)C)OC)C/C=C(/CCC(=O)OCCN1CCOCC1)\C
• Canonical SMILES: COc1c(C/C=C(/CCC(=O)OCCN2CCOCC2)\C)c(O)c2c(c1C)C(OCCN1CCOCC1)OC2=O
• InChI: InChI=1S/C29H42N2O9/c1-20(5-7-23(32)38-18-12-30-8-14-36-15-9-30)4-6-22-26(33)25-24(21(2)27(22)35-3)29(40-28(25)34)39-19-13-31-10-16-37-17-11-31/h4,29,33H,5-19H2,1-3H3/b20-4+
• InChIKey: XKAOBWLSKUSFOB-LRNAUUFOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(morpholin-4-yl)ethyl (4E)-6-{4-hydroxy-6-methoxy-7-methyl-1-[2-(morpholin-4-yl)ethoxy]-3-oxo-1,3-dihydro-2-benzofuran-5-yl}-4-methylhex-4-enoate
• IUPAC Traditional name: 2-(morpholin-4-yl)ethyl (4E)-6-{4-hydroxy-6-methoxy-7-methyl-1-[2-(morpholin-4-yl)ethoxy]-3-oxo-1H-2-benzofuran-5-yl}-4-methylhex-4-enoate
• Synonyms: (4E)-6-[1,3-Dihydro-4-hydroxy-6-methoxy-7-methyl-1-[2-(4-morpholinyl)ethoxy]-3-oxo-5-isobenzofuranyl]-4-methyl-4-hexenoic Acid 2-(4-Morpholinyl)ethyl Ester; Mycophenolate mofetil Imp. B (EP); 1-[2-(4-Morpholinyl)ethoxy] Mycophenolate Mofetil

Database IDs

• CAS Number: 1094322-91-4
• PubChem SID: 164230738
• PubChem CID: 25144924

CALCULATED PROPERTIES

• Acid pKa: 9.661161
• H Acceptors: 9
• H Donor: 1
• LogD (pH = 5.5): 1.8453934
• LogD (pH = 7.4): 3.4844346
• Log P: 3.5526822
• Molar Refractivity: 149.9708 cm^3
• Polarizability: 58.156517 Å^3
• Polar Surface Area: 116.23 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - M725050

Mycophenolate Mofetil (M831450) impurity present in the process for the purification of Mycophenolate mofetil upon esterified of mycophenolic acid with 2-morpholinoethanol.

REFERENCES

• Nelson, P.H., et al.: J. Med. Chem., 33, 833 (1990)