Phosphoric Acid → 7-Acetoacetamido-3-(5-methyl-1,3,4-oxadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid

HRID 596793Notes

Reaction equation

HRID 596793 reaction equation
[C:1]([NH:7][CH:8]1[C:23](=[O:24])[N:10]2[C:11]([C:20]([OH:22])=[O:21])=[C:12]([CH2:15]OC(=O)C)[CH2:13][S:14][C@H:9]12)(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].C(=O)([O-])O.[Na+].[CH3:30][C:31]1[O:35][C:34]([SH:36])=[N:33][N:32]=1.P([O-])([O-])([O-])=O.P(=O)(O)(O)O>O.C(OCC)(=O)C>[C:1]([NH:7][CH:8]1[C:23](=[O:24])[N:10]2[C:11]([C:20]([OH:22])=[O:21])=[C:12]([CH2:15][S:36][C:34]3[O:35][C:31]([CH3:30])=[N:32][N:33]=3)[CH2:13][S:14][C@H:9]12)(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4]

Participants

8

Reactant 5

HCID 1004Phosphoric AcidHCID 1061PhosphateHCID 516892Sodium BicarbonateHCID 88715150HCID 88715150, compoundHCID 178434159HCID 178434159, compound

Product 1

HCID 1317106647-Acetoacetamido-3-(5-methyl-1,3,4-oxadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acidYield 48%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 0.178 g. of 7-acetoacetamido-3-acetoxymethyl-3-cephem-4-carboxylic acid, 0.42 g. of sodium hydrogen carbonate, 0.64 g. of 5-methyl-1,3,4-oxadiazole-2-thiol and 10 ml. of a phosphate buffer of pH 6.4 is heated at 55°-60° C for 16 hours. After cooling, the reaction mixture is shaken with ethyl acetate and the water layer is taken, adjusted to pH 2 with 50 % phosphoric acid and extracted three times with ethyl acetate. The extracts are pooled, washed with water and dehydrated over sodium sulfate. Then, the solvent is distilled off and ether is added to the residue, whereupon 0.10 g. (48 %) of 7-acetoacetamido-3-(5-methyl-1,3,4-oxadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid is obtained as crystals melting at 80°-85° C(decomp.).

Workup

  1. additionA mixture of 0.178 g
  2. temperatureAfter cooling
  3. extractionextracted three times with ethyl acetate
  4. washwashed with water
  5. distillationThen, the solvent is distilled off
  6. additionether is added to the residue, whereupon 0.10 g

Sources & evidence

ORD record
ord-4d48a21fcf174b318f54198c022910f4
Source dataset
uspto-grants-1977_03
Patent number
US04012379

Reaction notes

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