Acetic Anhydride → Fosmidomycin

Formic acid (1.0 ml.) was added dropwise to acetic anhydride (1.2 ml.) at ambient temperature with stirring. The stirring was continued at the same temperature for 30 minutes and then 3-(N-hydroxyamino)propylphosphonic acid (1.51 g.) was added to the mixture. The reaction mixture was stirred at ambient temperature for 1.5 hours and concentrated under reduced pressure to given an oily residue, which was dissolved in ethanol (20 ml.). To the aqueous solution was added ethanolamine (0.61 g.) to precipitate an oil, which was separated by decantation and crystallized with ethanol (20 ml.) to give crystals. The crystals were separated by filtration, washed with ethanol and dried to give crystalline monoethanolamine salt of 3-(N-formyl-N-hydroxyamino)propylphosphonic acid (1.75 g.), a part (1.5 g.) of which was recrystallized from 90% aqueous ethanol to give the purified object compound (1.15 g). M.p. 139°-142° C.

1. stirringThe reaction mixture was stirred at ambient temperature for 1.5 hours
2. concentrationconcentrated under reduced pressure
3. dissolutionwas dissolved in ethanol (20 ml.)
4. additionTo the aqueous solution was added ethanolamine (0.61 g.)
5. customto precipitate an oil, which
6. customwas separated by decantation
7. customcrystallized with ethanol (20 ml.)
8. customto give crystals
9. customThe crystals were separated by filtration
10. washwashed with ethanol
11. customdried

ORD-Eintrag

ord-8bbfae82b73349da98f7cbfe609f6cb5

Quelldatensatz

uspto-grants-1980_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US04182758