Formic Acid → N,O-Diformyl,(S)-Isoserine

Temperature

0 °C

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).

1. customthe completion of reaction by H1 -NMR (approx. 2 hrs)
2. concentrationthe mixture was concentrated under vacuum at 40° C. to half of the original volume
3. addition250 ml of isopropanol was added slowly
4. temperaturewith simultaneous cooling
5. customcrystallization
6. filtrationThe product, N,O-diformyl-(S)-isoserine, was filtered
7. washwashed with isopropanol
8. custom-38° (1%, MeOH)

ORD record

ord-c612de9510ce4bb5bd0732941c8ca95d

Source dataset

uspto-grants-1995_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05442047