Reaktion #81614

Reaktionsgleichung

ethyl acetate

Sodium borohydride

3-[2-[(4-chlorophenyl)sulphonylamino]ethyl]-5-(4-fluorobenzoyl)benzenepropanoic acid

hydrochloric acid

→

title compound

Ausbeute 71.7%

3-[2-[(4-Chlorophenyl)sulphonylamino]ethyl]-5-[(4-fluorophenyl)hydroxymethyl]benzenepropanoic acid

Ausbeute 71.7%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture was stirred for 1 hour
2. 2
   SonstigeThe organic layer was separated
3. 3
   Waschenwashed with water
4. 4
   Trocknendried (MgSO4)
5. 5
   SonstigeThe solvent was evaporated
6. 6
   Sonstigethe residue was chromatographed on silica gel
7. 7
   WaschenThe column was eluted with hexane/ethyl acetate (5:1)
8. 8
   Temperaturgradually increasing the polarity
9. 9
   Sonstigeto give a ratio of 10:90:1
10. 10
    Sonstigeevaporated

Vorschrift

Sodium borohydride (0.077 g) was added portionwise to a suspension of 3-[2-[(4-chlorophenyl)sulphonylamino]ethyl]-5-(4-fluorobenzoyl)benzenepropanoic acid (0.50 g) in ethanol (12 ml), and the resulting solution was stirred at room temperature for 18 hours. 2N hydrochloric acid (5 ml) was added dropwise followed by ethyl acetate (50 ml), and the mixture was stirred for 1 hour. The organic layer was separated, washed with water and dried (MgSO4). The solvent was evaporated and the residue was chromatographed on silica gel. The column was eluted with hexane/ethyl acetate (5:1), followed by hexane/ethyl acetate/acetic acid (50:50:1), gradually increasing the polarity to give a ratio of 10:90:1. The product fractions were combined and evaporated to give the title compound as a gum (0.36 g), Rf 0.45 (SS 15). Found: C,58.58; H,4.71; N,2.65. C24H23ClFNO5S requires C,58.59; H,4.71; N,2.85%.

Quelle