Reaktion #59833

ord-9c9e82c92ca4405983546cd6640077cf

Reaktionsgleichung

O=S(=O)([O-])O.[K+]
potassium hydrogen sulfate
[H-].[Na+]
sodium hydride
Cc1ccc(C(=O)c2cccn2C/C=C/c2ccc(COC[C@@H](O)C(=O)O)cc2)cc1
compound
Cc1ccc(C(=O)c2cccn2C/C=C/c2ccc(COC[C@@H](O)C(=O)O)cc2)cc1
(2R)-2-Hydroxy-3-[(4-{(1E)-3-[2-(4-methylbenzoyl)-1H-pyrrol-1-yl]prop-1-en-1-yl}benzyl)oxy]propionic acid
CI
methyl iodide
CO[C@H](COCc1ccc(/C=C/Cn2cccc2C(=O)c2ccc(C)cc2)cc1)C(=O)O
title compound
CO[C@H](COCc1ccc(/C=C/Cn2cccc2C(=O)c2ccc(C)cc2)cc1)C(=O)O
(2R)-2-Methoxy-3 -[(4-{(1E)-3 -[2-(4-methylbenzoyl)-1H-pyrrol-1-yl]prop-1-en-1-yl}benzyl)oxy]propionic acid

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Temperaturcooling
  2. 2
    workup.STIRRINGThe mixture was stirred at room temperature for 2 hours
  3. 3
    Extraktionthe mixture was extracted with ethyl acetate
  4. 4
    WaschenThe organic layer was washed with saturated saline
  5. 5
    Trocknendried over anhydrous magnesium sulfate
  6. 6
    Sonstigethe solvent was evaporated under reduced pressure

Vorschrift

The compound of Example 69-2 (24 mg, 0.05 mmol) was dissolved in THF (1 ml), and thereto was added sodium hydride (5 mg, 0.11 mmol) under ice-cooling. The mixture was warmed to room temperature, and stirred for 30 minutes, and thereto was added methyl iodide (15 mg, 0.11 mmol). The mixture was stirred at room temperature for 2 hours, and thereto was added a 5% aqueous potassium hydrogen sulfate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give the title compound.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07425642B2uspto-grants-2008_09