(2S)-3-methyl-2-(naphthalene-2-sulfonamido)butanoic acid

• ChemBase ID: 174965
• Molecular Formular: C15H17NO4S
• Molecular Mass: 307.36478
• Monoisotopic Mass: 307.08782903
• SMILES: c1ccc2c(c1)cc(cc2)S(=O)(=O)N[C@@H](C(C)C)C(=O)O
• Canonical SMILES: CC([C@@H](C(=O)O)NS(=O)(=O)c1ccc2c(c1)cccc2)C
• InChI: InChI=1S/C15H17NO4S/c1-10(2)14(15(17)18)16-21(19,20)13-8-7-11-5-3-4-6-12(11)9-13/h3-10,14,16H,1-2H3,(H,17,18)/t14-/m0/s1
• InChIKey: GFCPZHIUZCLSNZ-AWEZNQCLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-3-methyl-2-(naphthalene-2-sulfonamido)butanoic acid
• IUPAC Traditional name: (2S)-3-methyl-2-(naphthalene-2-sulfonamido)butanoic acid
• Synonyms: N-(2-Naphthalenylsulfonyl)-D-valine; β-Naphthalenesulfonyl-D-valine

Database IDs

• CAS Number: 182227-17-4
• PubChem SID: 164230875
• PubChem CID: 730259

CALCULATED PROPERTIES

• Acid pKa: 3.466387
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.7026966
• LogD (pH = 7.4): -0.65930337
• Log P: 2.7266722
• Molar Refractivity: 79.1369 cm^3
• Polarizability: 32.822094 Å^3
• Polar Surface Area: 83.47 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Methyl tert-Butyl Ether

DETAILS

Toronto Research Chemicals - N359260

Used in the synthesis of spirofused azetidinone as cholesterol absorption inhibitor.