Reaktion #747759

Reaktionsgleichung

(R)-2-(tert-butyldimethylsilanyloxy)-1-(2-iodophenyl)-ethylamine

EDCl

2-iodobenzoic acid

HOBt

→

title compound

N—[(R)-2-(tert-Butyldimethylsilanyloxy)-1-(2-iodophenyl)-ethyl]-2-iodobenzamide

Lösungsmittel

triethylamine

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe mixture is stirred at RT for 20 min
2. 2
   workup.STIRRINGstirring
3. 3
   workup.WAITis continued for 18 h
4. 4
   SonstigeThe solvent is removed under reduced pressure and water
5. 5
   workup.ADDITIONis added to the residue
6. 6
   ExtraktionThe mixture is extracted with EtOAc
7. 7
   Waschenthe organic phase is washed with brine
8. 8
   Trocknendried over magnesium sulfate
9. 9
   SonstigeThe solvent is removed under reduced pressure
10. 10
    Sonstigethe residue purified by flash chromatography

Vorschrift

To a solution of 2-iodobenzoic acid (0.66 g, 2.65 mmol) in THF (90 mL) is added HOBt (0.71 g, 5.3 mmol). After the mixture is stirred at RT for 15 min, EDCl (1.0 g, 5.3 mmol) is added followed by triethylamine (1.1 mL). The mixture is stirred at RT for 20 min then (R)-2-(tert-butyldimethylsilanyloxy)-1-(2-iodophenyl)-ethylamine (Org. Lett. 6, 513 (2004)) (1.0 g, 2.65 mmol) is added and stirring is continued for 18 h. The solvent is removed under reduced pressure and water is added to the residue. The mixture is extracted with EtOAc and the organic phase is washed with brine and dried over magnesium sulfate. The solvent is removed under reduced pressure and the residue purified by flash chromatography using a gradient of 0-60% EtOAc/hexane as eluent to give the title compound as a yellow solid.

Quelle