(2S)-2-{[(benzyloxy)carbonyl]amino}-3,3-dimethylbutanoic acid

• ChemBase ID: 50810
• Molecular Formular: C14H19NO4
• Molecular Mass: 265.30496
• Monoisotopic Mass: 265.13140809
• SMILES: C(=O)(N[C@H](C(=O)O)C(C)(C)C)OCc1ccccc1
• Canonical SMILES: O=C(N[C@@H](C(C)(C)C)C(=O)O)OCc1ccccc1
• InChI: InChI=1S/C14H19NO4/c1-14(2,3)11(12(16)17)15-13(18)19-9-10-7-5-4-6-8-10/h4-8,11H,9H2,1-3H3,(H,15,18)(H,16,17)/t11-/m1/s1
• InChIKey: NSVNKQLSGGKNKB-LLVKDONJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{[(benzyloxy)carbonyl]amino}-3,3-dimethylbutanoic acid
• IUPAC Traditional name: (2S)-2-{[(benzyloxy)carbonyl]amino}-3,3-dimethylbutanoic acid
• Synonyms: 3-Methyl-N-[(phenylmethoxy)carbonyl]-L-valine; N-Carbobenzoxy-(S)-tert-leucine; 2S-Benzyloxycarbonylamino-3,3-dimethylbutyric Acid; Z-L-tert-Leucine; Benzyloxycarbonyl-L-tert-leucine; N-(Benzyloxycarbonyl)-L-tert-butylglycine; N-Benzyloxycarbonyl-L-tert-leucine; N-Benzyloxycarbonyl-tert-leucine; Cbz-L-tert-Leucine; Z-tert-Leu-OH; N-Benzyloxycarbonyl-L-tert-leucine; (2S)-2-{[(Benzyloxy)carbonyl]amino}-3,3-dimethylbutanoic acid; N-苄氧基羰基-L-叔-亮氨酸

Database IDs

• CAS Number: 62965-10-0; 59269-54-4
• MDL Number: MFCD00137411
• PubChem SID: 162055573
• PubChem CID: 9899995

CALCULATED PROPERTIES

• Acid pKa: 3.9570458
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.298633
• LogD (pH = 7.4): -0.33379126
• Log P: 2.8493955
• Molar Refractivity: 69.571 cm^3
• Polarizability: 27.495182 Å^3
• Polar Surface Area: 75.63 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Pale Yellow Thick Oil
• Melting Point: Oil
• Optical Rotation: -4 (c=1 in methanol)

Safety Information

• Storage Condition: Refrigerator
• Storage Warning: IRRITANT
• TSCA Listed: false; 否

Product Information

• Purity: >90%; 95+%; 99%

DETAILS

Toronto Research Chemicals - C227750

Leucine derivative used in the preparation of various pharmaceutical agents such as TRPV4 antagonists, HIV-1 protease inhibitors and serine protease inhibitors.

REFERENCES

• Perni, R.B. et al.: Bioorg. Med. Chem. Lett., 17, 3406 (2007)
• Ekegren, J.K. et al.: J. Med. Chem., 48, 8098 (2007)