Reaction #55414

Reaction equation

sodium hydroxide

7-amino-3-[1-(2-carbamoylethyl)tetrazol-5-ylthiomethyl]-3-cephem-4-carboxylic acid

sodium bicarbonate

methylmercaptoacetyl chloride

→

title compound

7-Methylmercaptoacetamido-3-[1-(2-carbamoylethyl)tetrazol-5-ylthiomethyl]-3-cephem-4-carboxylic acid

Solvents

acetone

acetone

Conditions

Workup

1. 1
   TemperatureTo a stirred, cooled (-20°) solution of 10.2 g
2. 2
   workup.ADDITIONAfter addition the reaction mixture
3. 3
   Temperatureis warmed to 25°
4. 4
   Extractionextracted with ether
5. 5
   TemperatureThe remaining aqueous phase is cooled
6. 6
   workup.ADDITIONof ethyl acetate is added
7. 7
   OtherThe layers are separated
8. 8
   Extractionthe aqueous phase is extracted twice more with ethyl acetate
9. 9
   DryingThe combined extracts are dried (MgSO4)
10. 10
    Otherevaporated to dryness

Procedure

To a stirred, cooled (-20°) solution of 10.2 g. (0.026 mol.) of 7-amino-3-[1-(2-carbamoylethyl)tetrazol-5-ylthiomethyl]-3-cephem-4-carboxylic acid in 220 ml. of 3% sodium bicarbonate and 220 ml. of acetone is dropwise added a solution of 3.66 g. (0.029 mol.) of methylmercaptoacetyl chloride in 52 ml. of acetone, during which time the pH of the reaction mixture is maintained at 8.0 by addition of 10% sodium hydroxide. After addition the reaction mixture is stirred an additional 20 minutes at -15°, then is warmed to 25° and extracted with ether. The remaining aqueous phase is cooled, 250 ml. of ethyl acetate is added and the slurry is acidified with 3N hydrochloric acid. The layers are separated and the aqueous phase is extracted twice more with ethyl acetate. The combined extracts are dried (MgSO4) and evaporated to dryness to yield the title compound.

Source