Acetic Anhydride → 7beta-Formamido-3-(3-oxobutyryloxymethyl)-3-cephem-4-carboxylic acid

HRID 978416Notes

Reaction equation

HRID 978416 reaction equation
[NH2:1][C@@H:2]1[C:20](=[O:21])[N:4]2[C:5]([C:17]([OH:19])=[O:18])=[C:6]([CH2:9][O:10][C:11](=[O:16])[CH2:12][C:13](=[O:15])[CH3:14])[CH2:7][S:8][C@H:3]12.[C:22](OC(=O)C)(=[O:24])C>C(O)=O>[CH:22]([NH:1][C@@H:2]1[C:20](=[O:21])[N:4]2[C:5]([C:17]([OH:19])=[O:18])=[C:6]([CH2:9][O:10][C:11](=[O:16])[CH2:12][C:13](=[O:15])[CH3:14])[CH2:7][S:8][C@H:3]12)=[O:24]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 117819897beta-Amino-3(3-oxobutyryloxymethyl)-3-cephem-4-carboxylic acid

Product 1

HCID 885003007beta-Formamido-3-(3-oxobutyryloxymethyl)-3-cephem-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

In 60 ml of formic acid is dissolved 3.2 g of 7β-amino-3-(3-oxobutyryloxymethyl)-3-cephem-4-carboxylic acid and the solution is cooled to 0°-5° C. With stirring, 20 ml of acetic anhydride is added dropwise to the solution during 30 minutes. The mixture is stirred at the same temperature for 30 minutes and then at room temperature for 1 hour. The solvent is evaporated off under reduced pressure and the residue is dissolved in methyl ethyl ketone. The solution is washed with water and saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent is then evaporated off under reduced pressure and a diisopropylether-hexane mixture is added to the residue to bring about solidification. The solid is then collected by filtration to give 3.1 g of the above-identified compound as a light-yellow powder.

Workup

  1. temperaturethe solution is cooled to 0°-5° C
  2. stirringThe mixture is stirred at the same temperature for 30 minutes
  3. customThe solvent is evaporated off under reduced pressure
  4. dissolutionthe residue is dissolved in methyl ethyl ketone
  5. washThe solution is washed with water and saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent is then evaporated off under reduced pressure
  8. additiona diisopropylether-hexane mixture is added to the residue
  9. filtrationThe solid is then collected by filtration

Sources & evidence

ORD record
ord-7de0e93f40fd438f8e085f1cb433a855
Source dataset
uspto-grants-1987_05
Patent number
US04665065

Reaction notes

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