(2S)-2-{[(2S)-1-(benzyloxy)-1-oxo-4-phenylbutan-2-yl]amino}propanoic acid

• ChemBase ID: 161731
• Molecular Formular: C20H23NO4
• Molecular Mass: 341.40092
• Monoisotopic Mass: 341.16270822
• SMILES: c1(CC[C@@H](C(=O)OCc2ccccc2)N[C@@H](C)C(=O)O)ccccc1
• Canonical SMILES: O=C([C@@H](N[C@H](C(=O)O)C)CCc1ccccc1)OCc1ccccc1
• InChI: InChI=1S/C20H23NO4/c1-15(19(22)23)21-18(13-12-16-8-4-2-5-9-16)20(24)25-14-17-10-6-3-7-11-17/h2-11,15,18,21H,12-14H2,1H3,(H,22,23)/t15-,18-/m0/s1
• InChIKey: RLFXILKNOGXPCT-YJBOKZPZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{[(2S)-1-(benzyloxy)-1-oxo-4-phenylbutan-2-yl]amino}propanoic acid
• IUPAC Traditional name: (2S)-2-{[(2S)-1-(benzyloxy)-1-oxo-4-phenylbutan-2-yl]amino}propanoic acid
• Synonyms: α-[[(1S)-1-carboxyethyl]amino]benzenebutanoic Acid Mono(phenylmethyl) Ester; (2S)-2-[N-[(1S)-1-(benzyloxycarbonyl)-3-phenylpropyl]amino]propionic Acid; N-[1-(S)-Benzyloxycarbonyl-3-phenylpropyl]-L-alanine

Database IDs

• CAS Number: 89371-42-6
• PubChem SID: 162255866
• PubChem CID: 14804503

CALCULATED PROPERTIES

• Acid pKa: 3.162666
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 2.2286248
• LogD (pH = 7.4): 0.80063766
• Log P: 2.4624848
• Molar Refractivity: 94.4521 cm^3
• Polarizability: 37.450935 Å^3
• Polar Surface Area: 75.63 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate; Methanol
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - B286005

Intermediate in the preparation of Imidaprilat

REFERENCES

• Bennion, C., et al.: J. Med. Chem., 34, 439 (1991)