Pyridine → propan-2-yl 5-fluoro-4-[(Z)-furan-2-ylmethylideneamino]oxy-2,6-dioxo-1,3-diazinane-5-carboxylate

HRID 485314Notes

Reaction equation

HRID 485314 reaction equation
[F:1][C:2]1([C:11]([O:13][CH:14]([CH3:16])[CH3:15])=[O:12])[CH:7]([OH:8])[NH:6][C:5](=[O:9])[NH:4][C:3]1=[O:10].N1C=CC=CC=1.C(OC(=O)C)(=O)C.[CH:30](=[N:36]/O)/[C:31]1[O:35][CH:34]=[CH:33][CH:32]=1>CC(C)=O>[F:1][C:2]1([C:11]([O:13][CH:14]([CH3:16])[CH3:15])=[O:12])[CH:7]([O:8]/[N:36]=[CH:30]\[C:31]2[O:35][CH:34]=[CH:33][CH:32]=2)[NH:6][C:5](=[O:9])[NH:4][C:3]1=[O:10]

Participants

6

Reactant 4

HCID 1049Pyridine2×HCID 7918Acetic AnhydrideHCID 5354160HCID 5354160, compoundHCID 12901281HCID 12901281, compound

Product 1

HCID 88687967propan-2-yl 5-fluoro-4-[(Z)-furan-2-ylmethylideneamino]oxy-2,6-dioxo-1,3-diazinane-5-carboxylateYield 32.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

In 50 ml of acetone was dissolved 20.0 g (85.4 mmol) of isopropyl 5-fluoro-6-hydroxy-1,2,3,4,5,6-hexahydro-2,4-dioxopyrimidine-5-carboxylate, and 8.78 g (111.0 mmol) of pyridine and 8.65 g (93.9 mmol) of acetic anhydride were added to the solution, followed by stirring under ice-cooling for 3 hours and subsequently at room temperature for 16 hours. The solvent was disttiled off under reduced pressure, and the acetylated compound, which precipitates after the addition of water, was recovered by filtration, washed with water and dried. One-half its amount and 5.70 g (51.2 mmol) of (Z)-furfuraldoxime were dissolved in 30 ml of pyridineacetone (pyridine:acetone=2.1), and the solution was stirred at 60° C. for 15 hours. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography with hexane-ethyl acetate changing gradually the mixing ratio from (9:1) to (1:2) to yield 5.5 g of 5-fluoro-6-[(Z)-furfurylideneaminooxy]-5-isopropyloxycarbonyl-1,2,3,4,5,6-hexahydro-2,4-dioxopyrimidine. m.p. 131°-134° C.

Workup

  1. additionwere added to the solution
  2. customthe acetylated compound, which precipitates
  3. additionafter the addition of water
  4. filtrationwas recovered by filtration
  5. washwashed with water
  6. customdried
  7. stirringthe solution was stirred at 60° C. for 15 hours
  8. distillationThe solvent was distilled off under reduced pressure
  9. customthe residue was purified by silica gel column chromatography with hexane-ethyl acetate changing gradually the mixing ratio from (9:1) to (1:2)

Sources & evidence

ORD record
ord-d49433a840db4c06be021b2d2711b321
Source dataset
uspto-grants-1985_08
Patent number
US04536504

Reaction notes

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