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

• ChemBase ID: 173441
• Molecular Formular: C15H21NO5
• Molecular Mass: 295.33094
• Monoisotopic Mass: 295.14197278
• SMILES: c1c(ccc(c1)C[C@H](N(C(=O)OC(C)(C)C)C)C(=O)O)O
• Canonical SMILES: CN([C@H](C(=O)O)Cc1ccc(cc1)O)C(=O)OC(C)(C)C
• InChI: InChI=1S/C15H21NO5/c1-15(2,3)21-14(20)16(4)12(13(18)19)9-10-5-7-11(17)8-6-10/h5-8,12,17H,9H2,1-4H3,(H,18,19)/t12-/m0/s1
• InChIKey: APVBZIOLJVJCLT-LBPRGKRZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{[(tert-butoxy)carbonyl](methyl)amino}-3-(4-hydroxyphenyl)propanoic acid
• IUPAC Traditional name: (2S)-2-[(tert-butoxycarbonyl)(methyl)amino]-3-(4-hydroxyphenyl)propanoic acid
• Synonyms: N-[(1,1-Dimethylethoxy)carbonyl]-N-methyl-L-tyrosine; N-tert-Butoxycarbonyl-N-methyl-L-tyrosine; N-Methyl-N-t-butoxycarbonyl-L-tyrosine

Database IDs

• CAS Number: 82038-34-4
• PubChem SID: 164229351
• PubChem CID: 7019889

CALCULATED PROPERTIES

• Acid pKa: 3.8379662
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.8242457
• LogD (pH = 7.4): -0.7580908
• Log P: 2.489823
• Molar Refractivity: 76.8669 cm^3
• Polarizability: 29.971434 Å^3
• Polar Surface Area: 87.07 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Ethyl Acetate; Methanol
• Apperance: Colourless Oil

DETAILS

Toronto Research Chemicals - M294435

Used in the preparation of tyrosyl derivatives as P2X7 receptor modulators.

REFERENCES

• Morikawa, A., et al.: J. Med. Chem., 32, 46 (1989)
• Colotta, F., et al.: Science, 261, 472 (1989)
• Khakh, B., et al.: Pharmacol. Rev., 53, 107 (1989)