(2R)-2-azido-3-methylbutanoic acid; cyclohexanamine

• ChemBase ID: 161036
• Molecular Formular: C11H22N4O2
• Molecular Mass: 242.31798
• Monoisotopic Mass: 242.17427596
• SMILES: C([C@H](C(=O)O)N=[N+]=[N-])(C)C.C1CCCC(C1)N
• Canonical SMILES: NC1CCCCC1.[N-]=[N+]=N[C@@H](C(=O)O)C(C)C
• InChI: InChI=1S/C6H13N.C5H9N3O2/c7-6-4-2-1-3-5-6;1-3(2)4(5(9)10)7-8-6/h6H,1-5,7H2;3-4H,1-2H3,(H,9,10)/t;4-/m.1/s1
• InChIKey: YMXXCNHHCIMTCV-FZSMXKCYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-azido-3-methylbutanoic acid; cyclohexanamine
• IUPAC Traditional name: (2R)-2-azido-3-methylbutanoic acid; cyclohexylamine
• Synonyms: (2S)-2-Azido-3-methylbutanoic Acid Cyclohexylammonium Salt; (S)-2-Azido-3-methylbutyric Acid Cyclohexylammonium Salt; (S)-2-Azido Isovaleric Acid Cyclohexylammonium Salt

Database IDs

• CAS Number: 1217462-63-9
• PubChem SID: 162255171
• PubChem CID: 71313592

CALCULATED PROPERTIES

• Acid pKa: 3.799715
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -0.5805063
• LogD (pH = 7.4): -2.140549
• Log P: 1.2360102
• Molar Refractivity: 34.1279 cm^3
• Polarizability: 12.847862 Å^3
• Polar Surface Area: 66.73 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A854700

(S)-2-Azido Isovaleric Acid is an intermediate in the synthesis of Valacyclovir (V085000).

REFERENCES

• Gupta, R., et al.: J. Infect. Dis., 190, 1374 (2004)
• McGuigan, C., et al.: Bioorg. Med. Chem. Lett., 18, 4364 (2004)