(2R)-3-methyl-2-{[methyl({[2-(propan-2-yl)-1,3-thiazol-4-yl]methyl})carbamoyl]amino}butanoic acid

• ChemBase ID: 173847
• Molecular Formular: C14H23N3O3S
• Molecular Mass: 313.41572
• Monoisotopic Mass: 313.14601261
• SMILES: C([C@@H](NC(=O)N(Cc1csc(n1)C(C)C)C)C(=O)O)(C)C
• Canonical SMILES: CN(C(=O)N[C@@H](C(=O)O)C(C)C)Cc1csc(n1)C(C)C
• InChI: InChI=1S/C14H23N3O3S/c1-8(2)11(13(18)19)16-14(20)17(5)6-10-7-21-12(15-10)9(3)4/h7-9,11H,6H2,1-5H3,(H,16,20)(H,18,19)/t11-/m1/s1
• InChIKey: OSQWRZICKAOBFA-LLVKDONJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-3-methyl-2-{[methyl({[2-(propan-2-yl)-1,3-thiazol-4-yl]methyl})carbamoyl]amino}butanoic acid
• IUPAC Traditional name: (2R)-2-({[(2-isopropyl-1,3-thiazol-4-yl)methyl](methyl)carbamoyl}amino)-3-methylbutanoic acid
• Synonyms: N-[[Methyl[[2-(1-methylethyl)-4-thiazolyl]methyl]amino]carbonyl]-L-valine; N-[[N-Methyl-N-[(2-isopropyl]-4-thiazolyl)methyl)amino]carbonyl-L-valine Carboxylic Acid

Database IDs

• CAS Number: 154212-61-0
• PubChem SID: 164229757
• PubChem CID: 10805157

CALCULATED PROPERTIES

• Acid pKa: 4.0349793
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.5221942
• LogD (pH = 7.4): -1.1090293
• Log P: 1.8370538
• Molar Refractivity: 80.3477 cm^3
• Polarizability: 31.220226 Å^3
• Polar Surface Area: 82.53 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane
• Apperance: Light Yellow Oil

DETAILS

Toronto Research Chemicals - M314850

An intermediate in the synthesis of Ritonavir.

REFERENCES

• Hamada, Y., et al.: Bioorg. Med. Chem., 10, 4155 (2002)