Formic Acid → N,O-Diformyl,(S)-Isoserine
Reaktionsgleichung
[NH2:1][CH2:2][C@@H:3]([C:5]([OH:7])=[O:6])[OH:4].[CH:8](OC(=O)C)=[O:9].[CH:14](O)=[O:15]>>[CH:8]([NH:1][CH2:2][C@@H:3]([C:5]([O:7][CH:14]=[O:15])=[O:6])[OH:4])=[O:9]Komponenten
4
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
To a one liter round bottom flask containing 50 g of (S)-isoserine (0.476 mole) and 62.5 ml of formic acid was added in 30 min. a freshly prepared acetic formic anhydride solution * (5 eq.) at 0°-5° C. After examining the completion of reaction by H1 -NMR (approx. 2 hrs), the mixture was concentrated under vacuum at 40° C. to half of the original volume. 250 ml of isopropanol was added slowly with simultaneous cooling to effect crystallization. The slurry was stirred at 0° C. for one hour. The product, N,O-diformyl-(S)-isoserine, was filtered and washed with isopropanol. This afforded 64 g of N,O-diformyl-(S)-isoserine; 84% yield; m.p. 139.5°-141.5°; [a]D20 : -38° (1%, MeOH).