ethyl 2-{[(1R)-2-[(2S)-2-{[(4-cyanophenyl)methyl]carbamoyl}azetidin-1-yl]-1-cyclohexyl-2-oxoethyl]amino}acetate

• ChemBase ID: 179602
• Molecular Formular: C24H32N4O4
• Molecular Mass: 440.53528
• Monoisotopic Mass: 440.24235552
• SMILES: c1c(ccc(c1)CNC(=O)[C@@H]1CCN1C(=O)[C@H](NCC(=O)OCC)C1CCCCC1)C#N
• Canonical SMILES: CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)NCc1ccc(cc1)C#N)C1CCCCC1
• InChI: InChI=1S/C24H32N4O4/c1-2-32-21(29)16-26-22(19-6-4-3-5-7-19)24(31)28-13-12-20(28)23(30)27-15-18-10-8-17(14-25)9-11-18/h8-11,19-20,22,26H,2-7,12-13,15-16H2,1H3,(H,27,30)/t20-,22+/m0/s1
• InChIKey: OBOJZPLHHDGCCL-RBBKRZOGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 2-{[(1R)-2-[(2S)-2-{[(4-cyanophenyl)methyl]carbamoyl}azetidin-1-yl]-1-cyclohexyl-2-oxoethyl]amino}acetate
• IUPAC Traditional name: ethyl 2-{[(1R)-2-[(2S)-2-{[(4-cyanophenyl)methyl]carbamoyl}azetidin-1-yl]-1-cyclohexyl-2-oxoethyl]amino}acetate
• Synonyms: N-[(1R)-2-[(2S)-2-[[[(4-Cyanophenyl)methyl]amino]carbonyl]-1-azetidinyl]-1-cyclohexyl-2-oxoethyl]glycine Ethyl Ester; Ximelagatran Nitrile

Database IDs

• CAS Number: 260790-61-2
• PubChem SID: 164235512
• PubChem CID: 10225271

CALCULATED PROPERTIES

• Acid pKa: 14.204005
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.59651
• LogD (pH = 7.4): 1.8046961
• Log P: 1.8081164
• Molar Refractivity: 119.2656 cm^3
• Polarizability: 46.734154 Å^3
• Polar Surface Area: 111.53 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Chloroform; Dichloromethane; Ethyl Acetate; Methanol
• Apperance: Colourless Oil

DETAILS

Toronto Research Chemicals - X745015

Intermediate in the preparation of Ximelagatran.