4-methylbenzene-1-sulfonic acid benzyl (2S)-2-amino-4-phenylbutanoate

• ChemBase ID: 159806
• Molecular Formular: C24H27NO5S
• Molecular Mass: 441.53988
• Monoisotopic Mass: 441.16099397
• SMILES: c1(CC[C@@H](C(=O)OCc2ccccc2)N)ccccc1.c1cc(ccc1C)S(=O)(=O)O
• Canonical SMILES: O=C([C@H](CCc1ccccc1)N)OCc1ccccc1.Cc1ccc(cc1)S(=O)(=O)O
• InChI: InChI=1S/C17H19NO2.C7H8O3S/c18-16(12-11-14-7-3-1-4-8-14)17(19)20-13-15-9-5-2-6-10-15;1-6-2-4-7(5-3-6)11(8,9)10/h1-10,16H,11-13,18H2;2-5H,1H3,(H,8,9,10)/t16-;/m0./s1
• InChIKey: ZUUJKCXULBLVQX-NTISSMGPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-methylbenzene-1-sulfonic acid benzyl (2S)-2-amino-4-phenylbutanoate
• IUPAC Traditional name: toluenesulfonic acid benzyl (2S)-2-amino-4-phenylbutanoate
• Synonyms: (αS)-α-Amino-benzenebutanoic Acid Phenylmethyl Ester 4-Methylbenzenesulfonate; (2S)-2-Amino-benzenebutanoic Acid Benzyl Ester Tosylate Salt

Database IDs

• CAS Number: 117560-24-4
• PubChem SID: 162253941
• PubChem CID: 71313143

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 1.6682148
• LogD (pH = 7.4): 3.1653132
• Log P: 3.392551
• Molar Refractivity: 79.099 cm^3
• Polarizability: 31.437977 Å^3
• Polar Surface Area: 52.32 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solild
• Melting Point: 139-144°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - A591420

An intermediate in the preparation of Imidaprilat

REFERENCES

• Hayashi, K., et al.: J. Med. Chem., 32, 289 (1989)