Water → HCID 131710661, compound

HRID 596791Notes

Reaction equation

HRID 596791 reaction equation
[NH2:1][CH:2]1[C:22](=[O:23])[N:4]2[C:5]([C:19]([OH:21])=[O:20])=[C:6]([CH2:9][S:10][C:11]3[N:12]=[N+:13]([O-:18])[C:14]([CH3:17])=[CH:15][CH:16]=3)[CH2:7][S:8][C@H:3]12.C(=O)([O-])O.[Na+].O.[CH2:30]=[C:31]1[O:35][C:33](=[O:34])[CH2:32]1>CC(C)=O>[C:33]([NH:1][CH:2]1[C:22](=[O:23])[N:4]2[C:5]([C:19]([OH:21])=[O:20])=[C:6]([CH2:9][S:10][C:11]3[N:12]=[N+:13]([O-:18])[C:14]([CH3:17])=[CH:15][CH:16]=3)[CH2:7][S:8][C@H:3]12)(=[O:34])[CH2:32][C:31]([CH3:30])=[O:35]

Participants

6

Reactant 4

HCID 962WaterHCID 12661DiketeneHCID 516892Sodium BicarbonateHCID 706343047-Amino-3-(6-methyl-1-oxidopyridazin-3-yl)thiomethyl-3-cephem-4-carboxylic acid

Product 1

HCID 131710661HCID 131710661, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 0.354 g. of 7-amino-3-(6-methyl-1-oxidopyridazin-3-yl)thiomethyl-3-cephem-4-carboxylic acid, 0.42 g. of sodium hydrogen carbonate, 5 ml. of water and 5 ml. of acetone is cooled to 5° C and under stirring, 0.2 g. of diketene is added. The mixture is further stirred at room temperature for 30 minutes. The acetone is distilled off under reduced pressure and the residue is washed with ethyl acetate. The water layer is separated, brought to pH 2 with 50 % phosphoric acid, saturated with sodium chloride and extracted three times with ethyl acetate. The extracts are pooled, washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, concentrated and allowed to stand under cooling with ice. The resultant crystals are loosened with the addition of ether and recovered by suction-filtration. The procedure gives 7-acetoacetamido-3-(6-methyl-1-oxidopyridazin-3-yl) thiomethyl-3-cephem-4-carboxylic acid as crystals melting at 85°-87° C(decomp.). Yield 0.13 g. (30 %).

Workup

  1. additionA mixture of 0.354 g
  2. stirringThe mixture is further stirred at room temperature for 30 minutes
  3. distillationThe acetone is distilled off under reduced pressure
  4. washthe residue is washed with ethyl acetate
  5. customThe water layer is separated
  6. extractionextracted three times with ethyl acetate
  7. washwashed with a saturated aqueous solution of sodium chloride
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated
  10. temperatureunder cooling with ice
  11. additionThe resultant crystals are loosened with the addition of ether
  12. filtrationrecovered by suction-filtration

Sources & evidence

ORD record
ord-bb8acd012e9245d1b33858e8cd30c9b4
Source dataset
uspto-grants-1977_03
Patent number
US04012379

Reaction notes

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