3-Fluorocatechol → HCID 131717421, compound

HRID 892715Notes

Reaction equation

HRID 892715 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[C:3]=1[OH:9].CC(O[CH2:14][C:15]1[CH2:24][S:23][C@@H:18]2[C@H:19]([NH2:22])[C:20](=[O:21])[N:17]2[C:16]=1[C:25]([OH:27])=[O:26])=O>C(#N)C.B(F)(F)F>[NH2:22][CH:19]1[C:20](=[O:21])[N:17]2[C:16]([C:25]([OH:27])=[O:26])=[C:15]([CH2:14][C:7]3[CH:6]=[C:4]([OH:5])[C:3]([OH:9])=[C:2]([F:1])[CH:8]=3)[CH2:24][S:23][C@H:18]12

Participants

4

Reactant 2

HCID 677643-FluorocatecholHCID 4413287-Aminocephalosporanic acid

Product 1

HCID 131717421HCID 131717421, compound

Reagents, catalysts & solvents 1

HCID 11804697Acetonitrile--trifluoroborane (1/1)Solvent

Procedure

3-fluorocatechol 1.0 g was dissolved in 15% borontrifluoride acetonitrile solution. To the solution was added 7-aminocephalosporanic acid at 5° C. After the stirring for 40 hours at room temperature, the reaction mixture was concentrated to dryness and dissolved in water with the addition of sodium bicarbonate pH 7.0). The solution was washed with ethyl acetate and acidified with 6N-hydrochloric acid to pH The resulting crude crystals were collected by filtration and washed with water to give a mixture of the title compounds (1.74 g). The isolation and purification by high performance liquid chromatography (eluent; 3% acetonitrile in potassium phosphate buffer pH 6.0, column; ODS) gave the fractions of A and B as the order of elution. Each fraction was concentrated to dryness and the resulting solids were slurried in N,N-dimethylacetamide and filtered, respectively. Each DMAc solutions of title compounds A and B were submitted to the next step (Exp. 9 and Exp. 10) without further purification.

Workup

  1. concentrationthe reaction mixture was concentrated to dryness
  2. dissolutiondissolved in water with the addition of sodium bicarbonate pH 7.0)
  3. washThe solution was washed with ethyl acetate
  4. filtrationwere collected by filtration
  5. washwashed with water
  6. customto give
  7. customThe isolation and purification by high performance liquid chromatography (eluent; 3% acetonitrile in potassium phosphate buffer pH 6.0, column; ODS)
  8. customgave the fractions of A and B
  9. washas the order of elution
  10. concentrationEach fraction was concentrated to dryness
  11. filtrationfiltered
  12. customEach DMAc solutions of title compounds A and B were submitted to the next step (Exp. 9 and Exp. 10) without further purification

Sources & evidence

ORD record
ord-0f5e829afe1a4e14aea3c1f39ceffa9a
Source dataset
uspto-grants-1992_06
Patent number
US05120728

Reaction notes

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