(1R,2S)-1-[2-(2H5)ethoxyphenoxy]-3-hydroxy-1-phenylpropan-2-yl methanesulfonate

• ChemBase ID: 168362
• Molecular Formular: C18H22O6S
• Molecular Mass: 366.42868
• Monoisotopic Mass: 366.11370942
• SMILES: c1cc(c(cc1)O[C@@H]([C@H](CO)OS(=O)(=O)C)c1ccccc1)OCC
• Canonical SMILES: CCOc1ccccc1O[C@@H]([C@@H](OS(=O)(=O)C)CO)c1ccccc1
• InChI: InChI=1S/C18H22O6S/c1-3-22-15-11-7-8-12-16(15)23-18(14-9-5-4-6-10-14)17(13-19)24-25(2,20)21/h4-12,17-19H,3,13H2,1-2H3/t17-,18+/m0/s1
• InChIKey: WOCIBFTUEOPLOI-ZWKOTPCHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S)-1-[2-(^2H₅)ethoxyphenoxy]-3-hydroxy-1-phenylpropan-2-yl methanesulfonate
• IUPAC Traditional name: (1R,2S)-1-[2-(^2H₅)ethoxyphenoxy]-3-hydroxy-1-phenylpropan-2-yl methanesulfonate
• Synonyms: (2R,3S)-rel-3-(2-Ethoxyphenoxy)-3-phenyl-1,2-propanediol 2-Methanesulfonate; (2RS,3RS)-3-(2-Ethoxy-d5-phenoxy)-2-mesyloxy-3-phenyl-1-propanol

Database IDs

• CAS Number: 1189680-85-0
• PubChem SID: 162262494
• PubChem CID: 71316528

CALCULATED PROPERTIES

• Acid pKa: 14.515981
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 2.4146788
• LogD (pH = 7.4): 2.4146786
• Log P: 2.4146788
• Molar Refractivity: 93.0231 cm^3
• Polarizability: 37.837143 Å^3
• Polar Surface Area: 82.06 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate; Methanol
• Apperance: Off-White Solid

DETAILS

Toronto Research Chemicals - E892677

A labelled intermediate in the synthesis of Reboxetine (R142000).

REFERENCES

• Melloni, P., et al.: Tetrahedron, 41, 1393 (1985)