(2S)-2-{[(tert-butoxy)carbonyl]amino}-3-(4-{[(tert-butoxy)carbonyl]amino}phenyl)propanoic acid

• ChemBase ID: 162191
• Molecular Formular: C19H28N2O6
• Molecular Mass: 380.43542
• Monoisotopic Mass: 380.19473663
• SMILES: c1c(ccc(c1)C[C@@H](C(=O)O)NC(=O)OC(C)(C)C)NC(=O)OC(C)(C)C
• Canonical SMILES: O=C(OC(C)(C)C)Nc1ccc(cc1)C[C@@H](C(=O)O)NC(=O)OC(C)(C)C
• InChI: InChI=1S/C19H28N2O6/c1-18(2,3)26-16(24)20-13-9-7-12(8-10-13)11-14(15(22)23)21-17(25)27-19(4,5)6/h7-10,14H,11H2,1-6H3,(H,20,24)(H,21,25)(H,22,23)/t14-/m0/s1
• InChIKey: XDYRQXPKQWQRQK-AWEZNQCLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{[(tert-butoxy)carbonyl]amino}-3-(4-{[(tert-butoxy)carbonyl]amino}phenyl)propanoic acid
• IUPAC Traditional name: (2S)-2-[(tert-butoxycarbonyl)amino]-3-{4-[(tert-butoxycarbonyl)amino]phenyl}propanoic acid
• Synonyms: N-[(1,1-Dimethylethoxy)carbonyl]-4-[[(1,1-dimethylethoxy)carbonyl]amino]-D-phenylalanine; N,N'-Bis-Boc 4-Amino-L-phenylalanine

Database IDs

• PubChem SID: 162256326
• PubChem CID: 46780819

CALCULATED PROPERTIES

• Acid pKa: 3.622847
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 1.6073605
• LogD (pH = 7.4): 0.14574268
• Log P: 3.4806736
• Molar Refractivity: 100.2815 cm^3
• Polarizability: 38.63954 Å^3
• Polar Surface Area: 113.96 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - B414100

It is used for preparation of piperazine CCR-3 antagonists useful as anti-inflammatory agents.

REFERENCES

• Okada, J., et al.: Chem. Pharm. Bull., 28, 3315 (1980)