(2S)-1-[(2R)-2-amino-2-cyclohexylacetyl]-N-[(4-cyanophenyl)methyl]azetidine-2-carboxamide

• ChemBase ID: 159968
• Molecular Formular: C20H26N4O2
• Molecular Mass: 354.44604
• Monoisotopic Mass: 354.20557609
• SMILES: c1c(ccc(c1)CNC(=O)[C@@H]1CCN1C(=O)[C@H](N)C1CCCCC1)C#N
• Canonical SMILES: N[C@@H](C(=O)N1CC[C@H]1C(=O)NCc1ccc(cc1)C#N)C1CCCCC1
• InChI: InChI=1S/C20H26N4O2/c21-12-14-6-8-15(9-7-14)13-23-19(25)17-10-11-24(17)20(26)18(22)16-4-2-1-3-5-16/h6-9,16-18H,1-5,10-11,13,22H2,(H,23,25)/t17-,18+/m0/s1
• InChIKey: KSXWQVQZPDROFY-ZWKOTPCHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-1-[(2R)-2-amino-2-cyclohexylacetyl]-N-[(4-cyanophenyl)methyl]azetidine-2-carboxamide
• IUPAC Traditional name: (2S)-1-[(2R)-2-amino-2-cyclohexylacetyl]-N-[(4-cyanophenyl)methyl]azetidine-2-carboxamide
• Synonyms: (2S)-1-((2R)-2-Amino-2-cyclohexylacetyl)-N-[[4-cyanophenyl]methyl]-2-azetidinecarboxamide; 1-((2R)-2-Amino-2-cyclohexylacetyl)-N-(4'-cyanobenzyl)-2-L-azetidinecarboxamide

Database IDs

• PubChem SID: 162254103
• PubChem CID: 71313188

CALCULATED PROPERTIES

• Acid pKa: 14.383258
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -1.1335694
• LogD (pH = 7.4): 0.54199547
• Log P: 1.3948506
• Molar Refractivity: 98.8887 cm^3
• Polarizability: 38.583332 Å^3
• Polar Surface Area: 99.22 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Chloroform; Dichloromethane; Ethyl Acetate
• Apperance: Off-White Foam

DETAILS

Toronto Research Chemicals - A603660

Intermediate in the preparation of Ximelagatran.