Phosgene → Methyl 2-isocyano-3-phenylpropanoate

Reaktionsgleichung

C(Cl)(Cl)=O.[CH3:5][O:6][C:7](=[O:19])[C@H:8]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[NH:9][CH:10]=O.CN1CCOCC1>C(Cl)Cl>[CH3:5][O:6][C:7](=[O:19])[CH:8]([N+:9]#[C-:10])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

Versuchsvorschrift

A solution of phosgene (5.2 g, 0.052 mole) in dry methylene chloride (45 ml) is added dropwise to a stirred solution of N-formylphenylalanine methyl ester (10.0 g, 0.048 mole) and 1-methylmorpholine (13 g, 0.125 mole) in dry methylene chloride (25 ml) at -30° C. After completion of the addition the filtrate is concentrated under reduced pressure at room temperature. Benzene is added to the residue followed by filtration and concentration of the resulting solution. The residue is distilled to afford the title compound as a yellow oil, b.p. 97° C/0.3 mm, νmaxCHCl3 2150, 1746, 1595, 1578, 1489, 694 cm-1.