Reaktion #83205

Reaktionsgleichung

N-[2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-oxo-3-phenylpropyl]-L-serine, methyl ester

allyl trichloroacetimidate

trifluoromethanesulfonic acid

→

title compound

N-[2-(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-oxo-3-phenylpropyl]-O-2-propenyl-L-serine, methyl ester

Lösungsmittel

methylene chloride cyclohexane

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   WaschenWash with saturated aqueous sodium hydrogen carbonate, water
2. 2
   Trocknendry (MgSO4)
3. 3
   Sonstigeevaporate the solvent in vacuo
4. 4
   SonstigePurify by silica gel chromatography (gradient 20% ethyl acetate/hexane to 35% ethyl acetate/hexane)

Vorschrift

Dissolve N-[2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-oxo-3-phenylpropyl]-L-serine, methyl ester (25 g, 63 mmol) in methylene chloride/cyclohexane (1:1, 600 mL). Add allyl trichloroacetimidate (26 g, 128 mmol) and trifluoromethanesulfonic acid (5 mL), 56.6 mmol). Stir at room temperature under a nitrogen atmosphere for 5 hours and dilute with methylene chloride. Wash with saturated aqueous sodium hydrogen carbonate, water, dry (MgSO4) and evaporate the solvent in vacuo. Purify by silica gel chromatography (gradient 20% ethyl acetate/hexane to 35% ethyl acetate/hexane) to give the title compound; mp 95°-97° C.

Quelle