Reaktion #1778680

ord-bbaa47ca17a34d1bb739b957d53f8330

Reaktionsgleichung

NC(=O)[C@@H]1CC[C@H](c2ccc(OCc3ccccc3F)cc2)N1
(5R)-5-(4-{[(2-Fluorophenyl)methyl]oxy}phenyl)-L-prolinamide
CS(=O)(=O)O
methanesulfonic acid
→
CS(=O)(=O)O.NC(=O)[C@@H]1CC[C@H](c2ccc(OCc3ccccc3F)cc2)N1
title compound
CS(=O)(=O)O.NC(=O)[C@@H]1CC[C@H](c2ccc(OCc3ccccc3F)cc2)N1
(5R)-5-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-L-prolinamide methanesulfonate

Edukte

NC(=O)[C@@H]1CC[C@H](c2ccc(OCc3ccccc3F)cc2)N1
(5R)-5-(4-{[(2-Fluorophenyl)methyl]oxy}phenyl)-L-prolinamide
CS(=O)(=O)O
methanesulfonic acid

Reagenzien

Keine

Lösungsmittel

CCOC(C)=O
EtOAc

Reaktionsbedingungen

Temperatur
60°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.DISSOLUTIONto dissolve the compound
  2. 2
    workup.ADDITIONas soon as the acid was added
  3. 3
    SonstigeThe compound was isolated by filtration as a white solid
  4. 4
    Waschenwashed with EtOAc
  5. 5
    Sonstigedried in vacuo at 40° C. overweek-end

Vorschrift

EtOAc (6 ml) was added to (5R)-5-(4-{[(2-Fluorophenyl)methyl]oxy}phenyl)-L-prolinamide (E1, 300 mg) and this was heated at 60° C. for an hour to dissolve the compound. Then methanesulfonic acid (65 μl, 1.05 eq) was added to the solution and as soon as the acid was added, the solution went cloudy. This was then left to temperature cycle (0-40° C.) for 2 days. The compound was isolated by filtration as a white solid, washed with EtOAc and dried in vacuo at 40° C. overweek-end to afford 335 mg of the title compound.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08153681B2uspto-grants-2012_04