benzyl (2S)-2-{[(2S)-1-(tert-butoxy)-1-oxopropan-2-yl]amino}-4-phenylbutanoate

• ChemBase ID: 161732
• Molecular Formular: C24H31NO4
• Molecular Mass: 397.50724
• Monoisotopic Mass: 397.22530848
• SMILES: c1(CC[C@@H](C(=O)OCc2ccccc2)N[C@H](C(=O)OC(C)(C)C)C)ccccc1
• Canonical SMILES: O=C([C@@H](N[C@H](C(=O)OC(C)(C)C)C)CCc1ccccc1)OCc1ccccc1
• InChI: InChI=1S/C24H31NO4/c1-18(22(26)29-24(2,3)4)25-21(16-15-19-11-7-5-8-12-19)23(27)28-17-20-13-9-6-10-14-20/h5-14,18,21,25H,15-17H2,1-4H3/t18-,21-/m0/s1
• InChIKey: VJVSRTMPQCZFKD-RXVVDRJESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl (2S)-2-{[(2S)-1-(tert-butoxy)-1-oxopropan-2-yl]amino}-4-phenylbutanoate
• IUPAC Traditional name: benzyl (2S)-2-{[(2S)-1-(tert-butoxy)-1-oxopropan-2-yl]amino}-4-phenylbutanoate
• Synonyms: α-[[2-(1,1-Dimethylethoxy)-1-methyl-2-oxoethyl]amino]benzenebutanoic Acid Phenylmethyl Ester; N-[1-(S)-Benzyloxycarbonyl-3-phenylpropyl]-L-alanine tert-Butyl Ester

Database IDs

• CAS Number: 117560-14-2
• PubChem SID: 162255867
• PubChem CID: 14804501

CALCULATED PROPERTIES

• H Donor: 1
• LogD (pH = 5.5): 5.0708394
• LogD (pH = 7.4): 5.071721
• Log P: 5.0717325
• Molar Refractivity: 113.0268 cm^3
• Polarizability: 45.07609 Å^3
• Polar Surface Area: 64.63 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false
• H Acceptors: 3

PROPERTIES

Physical Property

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

DETAILS

Toronto Research Chemicals - B286010

Intermediate in the preparation of Imidaprilat

REFERENCES

• Hayashi, K., et al.: J. Med. Chem., 32, 289 (1989)
• Bennion, C., et al.: J. Med. Chem., 34, 439 (1989)