methyl (2S)-3-amino-2-{[(benzyloxy)carbonyl]amino}propanoate hydrochloride

• ChemBase ID: 173440
• Molecular Formular: C12H17ClN2O4
• Molecular Mass: 288.72738
• Monoisotopic Mass: 288.08768471
• SMILES: C(=O)([C@H](CN)NC(=O)OCc1ccccc1)OC.Cl
• Canonical SMILES: NC[C@@H](C(=O)OC)NC(=O)OCc1ccccc1.Cl
• InChI: InChI=1S/C12H16N2O4.ClH/c1-17-11(15)10(7-13)14-12(16)18-8-9-5-3-2-4-6-9;/h2-6,10H,7-8,13H2,1H3,(H,14,16);1H/t10-;/m0./s1
• InChIKey: OLOFLUKZNNTGBC-PPHPATTJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S)-3-amino-2-{[(benzyloxy)carbonyl]amino}propanoate hydrochloride
• IUPAC Traditional name: methyl (2S)-3-amino-2-{[(benzyloxy)carbonyl]amino}propanoate hydrochloride
• Synonyms: Methyl 2-(S)-[N-[(Benzyloxy)carbonyl]amino-3-aminopropionate, Hydrochloride; 3-Amino-N-[(phenylmethoxy)carbonyl]-L-alanine Methyl Ester Hydrochloride; Methyl 2-(S)-[N-Carbobenzyloxy]amino-3-aminopropionate, Hydrochloride

Database IDs

• CAS Number: 35761-27-4
• PubChem SID: 164229350
• PubChem CID: 13756825

CALCULATED PROPERTIES

• Acid pKa: 13.228659
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -1.9940548
• LogD (pH = 7.4): -0.3304411
• Log P: 0.5760018
• Molar Refractivity: 64.1476 cm^3
• Polarizability: 25.604292 Å^3
• Polar Surface Area: 90.65 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Solid
• Melting Point: 157-162°C dec.

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - M294430

Important building block for the synthesis of peptides containing DAP residues, e.g. bleomycins, edeines, tuberactinomycins.

REFERENCES

• Mendre, C., et al.: Tetrahedron Lett., 35, 5429 (1994)
• Shinagaga, S., et al.: J. Med. Chem., 30, 1458 (1994)