methyl (2S)-2-{[(tert-butoxy)carbonyl]amino}-4-carbamoylbutanoate

• ChemBase ID: 163222
• Molecular Formular: C11H20N2O5
• Molecular Mass: 260.2869
• Monoisotopic Mass: 260.13722175
• SMILES: NC(=O)CC[C@@H](C(=O)OC)NC(=O)OC(C)(C)C
• Canonical SMILES: COC(=O)[C@@H](NC(=O)OC(C)(C)C)CCC(=O)N
• InChI: InChI=1S/C11H20N2O5/c1-11(2,3)18-10(16)13-7(9(15)17-4)5-6-8(12)14/h7H,5-6H2,1-4H3,(H2,12,14)(H,13,16)/t7-/m0/s1
• InChIKey: QEKBLYGUGNADLL-ZETCQYMHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S)-2-{[(tert-butoxy)carbonyl]amino}-4-carbamoylbutanoate
• IUPAC Traditional name: methyl (2S)-2-[(tert-butoxycarbonyl)amino]-4-carbamoylbutanoate
• Synonyms: N2-[(1,1-Dimethylethoxy)carbonyl]-L-glutamine Methyl Ester; N2-Carboxy-glutamine N-tert-Butyl Methyl Ester; N-(tert-Butoxycarbonyl)-L-glutamine methyl ester

Database IDs

• CAS Number: 4976-88-9
• PubChem SID: 162257357
• PubChem CID: 10956293

CALCULATED PROPERTIES

• Acid pKa: 13.333398
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -0.100813344
• LogD (pH = 7.4): -0.10081364
• Log P: -0.10081319
• Molar Refractivity: 62.752 cm^3
• Polarizability: 25.006088 Å^3
• Polar Surface Area: 107.72 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - B690420

Protected Glutamine.

REFERENCES

• Webber, S., et al.: J. Med. Chem., 41, 2786 (1998)
• Castonguay, R., et al.: Bioorg. Med. Chem., 10, 4185 (1998)