3-amino-4-cyclobutyl-2-hydroxybutanamide hydrochloride

• ChemBase ID: 160176
• Molecular Formular: C8H17ClN2O2
• Molecular Mass: 208.68578
• Monoisotopic Mass: 208.09785547
• SMILES: NC(C(C(=O)N)O)CC1CCC1.Cl
• Canonical SMILES: NC(C(C(=O)N)O)CC1CCC1.Cl
• InChI: InChI=1S/C8H16N2O2.ClH/c9-6(7(11)8(10)12)4-5-2-1-3-5;/h5-7,11H,1-4,9H2,(H2,10,12);1H
• InChIKey: RPOOMVSVQPMDGI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-amino-4-cyclobutyl-2-hydroxybutanamide hydrochloride
• IUPAC Traditional name: 3-amino-4-cyclobutyl-2-hydroxybutanamide hydrochloride
• Synonyms: β-Amino-α-hydroxycyclobutanebutanamide Hydrochloride

Database IDs

• CAS Number: 394735-23-0
• PubChem SID: 162254311
• PubChem CID: 11344812

CALCULATED PROPERTIES

• Acid pKa: 12.615582
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): -3.6160889
• LogD (pH = 7.4): -2.1605191
• Log P: -0.78103596
• Molar Refractivity: 44.7544 cm^3
• Polarizability: 18.112263 Å^3
• Polar Surface Area: 89.34 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A611230

An intermediate in the preparation of HCV NS3 serine protease inhibitor Boceprevir (B674500).

REFERENCES

• Arasappan, A. et al.: J. Med. Chem., 52, 2806 (2009)
• Venkatraman, S. et al.: Bioorg. Med. Chem., 17, 4486 (2009)