Formic Acid → 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 give 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. customto give an oily residue, which
4. customto precipitate an oil, which
5. customwas separated by decantation
6. customcrystallized with ethanol (20 ml.)
7. customto give crystals
8. customThe crystals were separated by filtration
9. washwashed with ethanol
10. customdried

ORDレコード

ord-334762278649409e971e004259fabe42

出典データセット

uspto-grants-1980_06

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US04206156