(4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]azetidin-2-one

• ChemBase ID: 161779
• Molecular Formular: C31H27F2NO3
• Molecular Mass: 499.5477864
• Monoisotopic Mass: 499.19590017
• SMILES: c1cc(ccc1[C@H](CCC1C(=O)N([C@@H]1c1ccc(cc1)OCc1ccccc1)c1ccc(cc1)F)O)F
• Canonical SMILES: Fc1ccc(cc1)N1C(=O)C([C@H]1c1ccc(cc1)OCc1ccccc1)CC[C@@H](c1ccc(cc1)F)O
• InChI: InChI=1S/C31H27F2NO3/c32-24-10-6-22(7-11-24)29(35)19-18-28-30(34(31(28)36)26-14-12-25(33)13-15-26)23-8-16-27(17-9-23)37-20-21-4-2-1-3-5-21/h1-17,28-30,35H,18-20H2/t28?,29-,30+/m0/s1
• InChIKey: KEYVFYMGVLFXQK-YHCMTOLSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]azetidin-2-one
• IUPAC Traditional name: (4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]azetidin-2-one
• Synonyms: (3R,4S)-1-(4-Fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-[4-(phenylmethoxy)phenyl]-2-azetidinone; (3R,4S)-4-[(4-Benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-2-azetidinone; 1-(4-Fluorophenyl)-3(R)-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4(S)-(4-benzyloxyphenyl)azetidin-2-one; 4'-O-Benzyloxy Ezetimibe

Database IDs

• CAS Number: 163222-32-0
• PubChem SID: 162255914
• PubChem CID: 57582918

CALCULATED PROPERTIES

• Acid pKa: 14.443297
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 6.4294953
• LogD (pH = 7.4): 6.429495
• Log P: 6.4294953
• Molar Refractivity: 137.9566 cm^3
• Polarizability: 53.05433 Å^3
• Polar Surface Area: 49.77 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane
• Apperance: Off-White Solid

DETAILS

Toronto Research Chemicals - B286310

Protected Ezetimibe, used for the synthesis of related derivatives.

REFERENCES

• Raman, B., et al.: J. Pharm. Biomed. Anal., 52, 73 (2010)