Water → HCID 131710662, compound

HRID 596792Notes

Reaction equation

HRID 596792 reaction equation
[NH2:1][CH:2]1[C:23](=[O:24])[N:4]2[C:5]([C:20]([OH:22])=[O:21])=[C:6]([CH2:9][S:10][C:11]3[N+:16]([O-:17])=[N:15][C:14]([O:18][CH3:19])=[CH:13][CH:12]=3)[CH2:7][S:8][C@H:3]12.C(=O)([O-])[OH:26].[Na+:29].O.[CH2:31]=[C:32]1[O:36][C:34](=[O:35])[CH2:33]1>CC(C)=O>[OH2:17].[OH2:26].[OH2:35].[C:34]([NH:1][CH:2]1[C:23](=[O:24])[N:4]2[C:5]([C:20]([O-:22])=[O:21])=[C:6]([CH2:9][S:10][C:11]3[N+:16]([O-:17])=[N:15][C:14]([O:18][CH3:19])=[CH:13][CH:12]=3)[CH2:7][S:8][C@H:3]12)(=[O:35])[CH2:33][C:32]([CH3:31])=[O:36].[Na+:29]

Participants

6

Reactant 4

HCID 962WaterHCID 12661DiketeneHCID 516892Sodium BicarbonateHCID 70634219HCID 70634219, compound

Product 1

HCID 131710662HCID 131710662, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 0.392 g. of 7-amino-3-(3-methoxy-1-oxidopyridazin-6-yl)thiomethyl-3-cephem-4-carboxylic acid, 0.42 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, followed by further stirring at room temperature for 30 minutes. The acetone is distilled off and the residue is adjusted to pH 7 with 50 % phosphoric acid, washed with ethyl acetate and developed on a column of polystyrene resin (Amberlite XAD-2) with 5 % aqueous alcohol. The desired fractions are pooled and freeze-dried. The above procedure gives sodium 7-acetoacetamido-3-(3-methoxy-1-oxidopyridazin-6-yl)thiomethyl-3-cephem-4-carboxylate trihydrate as a powder with a faint brownish tinge. Yield 0.152 g. (32 %).

Workup

  1. additionA mixture of 0.392 g
  2. stirringby further stirring at room temperature for 30 minutes
  3. distillationThe acetone is distilled off
  4. washwashed with ethyl acetate
  5. customfreeze-dried

Sources & evidence

ORD record
ord-1aa210a4dac64e9caa06b6611547f375
Source dataset
uspto-grants-1977_03
Patent number
US04012379

Reaction notes

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