2-{[(tert-butoxy)carbonyl]amino}pentanoic acid

• ChemBase ID: 162625
• Molecular Formular: C10H19NO4
• Molecular Mass: 217.26216
• Monoisotopic Mass: 217.13140809
• SMILES: C(CC(NC(=O)OC(C)(C)C)C(=O)O)C
• Canonical SMILES: CCCC(C(=O)O)NC(=O)OC(C)(C)C
• InChI: InChI=1S/C10H19NO4/c1-5-6-7(8(12)13)11-9(14)15-10(2,3)4/h7H,5-6H2,1-4H3,(H,11,14)(H,12,13)
• InChIKey: INWOAUUPYIXDHN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{[(tert-butoxy)carbonyl]amino}pentanoic acid
• IUPAC Traditional name: 2-[(tert-butoxycarbonyl)amino]pentanoic acid
• Synonyms: N-[(1,1-Dimethylethoxy)carbonyl]norvaline; 2-tert-Butoxycarbonylaminopentanoic Acid; Boc-Nva-OH; rac-Boc Norvaline; 2-{[(tert-butoxy)carbonyl]amino}pentanoic acid

Database IDs

• CAS Number: 521286-38-4
• MDL Number: MFCD00270725
• PubChem SID: 162256760
• PubChem CID: 302433

CALCULATED PROPERTIES

• Acid pKa: 4.137726
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 0.50268763
• LogD (pH = 7.4): -1.1943688
• Log P: 1.8804772
• Molar Refractivity: 54.4953 cm^3
• Polarizability: 21.639687 Å^3
• Polar Surface Area: 75.63 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 103 - 105°C
• Hydrophobicity(logP): 2.23

Product Information

• Purity: 95%

DETAILS

Toronto Research Chemicals - B658900

Used in the preparation of 4-phenylpiperidine-substituted amino acid derivatives, particularly Valine amides, as modulators of chemokine receptor activity and their use in the treatment of inflammatory and autoimmune diseases.

REFERENCES

• Baraldi, P., et al.: J. Med. Chem., 46, 1318 (2003)
• Carson, K., et al.: Ann. Rep. Med. Chem., 39, 149 (2003)
• Jia, L., et al.: Br. J. Pharmacol., 147, 476 (2003)