tert-butyl (2S)-2-[(2-carbamoylethyl)amino]-3-methylbutanoate

• ChemBase ID: 176993
• Molecular Formular: C12H24N2O3
• Molecular Mass: 244.33056
• Monoisotopic Mass: 244.17869264
• SMILES: O(C(=O)[C@@H](NCCC(=O)N)C(C)C)C(C)(C)C
• Canonical SMILES: CC([C@@H](C(=O)OC(C)(C)C)NCCC(=O)N)C
• InChI: InChI=1S/C12H24N2O3/c1-8(2)10(14-7-6-9(13)15)11(16)17-12(3,4)5/h8,10,14H,6-7H2,1-5H3,(H2,13,15)/t10-/m0/s1
• InChIKey: XVZGFLXDPWEXRA-JTQLQIEISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tert-butyl (2S)-2-[(2-carbamoylethyl)amino]-3-methylbutanoate
• IUPAC Traditional name: tert-butyl (2S)-2-[(2-carbamoylethyl)amino]-3-methylbutanoate
• Synonyms: N-(3-Amino-3-oxopropyl)-L-valine 1,1-Dimethylethyl Ester; N-(3-Propanamido)-L-valine tert-Butyl Ester

Database IDs

• CAS Number: 192725-87-4
• PubChem SID: 164232903
• PubChem CID: 71751816

CALCULATED PROPERTIES

• Acid pKa: 16.607073
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -0.01605684
• LogD (pH = 7.4): 0.81583786
• Log P: 0.8492714
• Molar Refractivity: 65.4484 cm^3
• Polarizability: 26.347006 Å^3
• Polar Surface Area: 81.42 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

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

DETAILS

Toronto Research Chemicals - P759150

Intermediate in the preparation of Lopinavir metabolites.

REFERENCES

• Flosi, W., et al.: Bioorg. Med. Chem., 14, 6695 (2006)