Reaction #55411

Reaction equation

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

dimethylformamide

trifluoromethylmercaptoacetic acid

→

title compound

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

Solvents

triethylamine

Conditions

Workup

1. 1
   workup.ADDITIONA suspension of 3.85 g
2. 2
   OtherThe reaction mixture was evaporated to dryness and water and ethyl acetate
3. 3
   workup.ADDITIONwere added to the residue
4. 4
   OtherThe layers were separated
5. 5
   workup.ADDITIONethyl acetate was added to the aqueous phase and it
6. 6
   workup.ADDITIONwas acidified to pH 2.5 by addition of 6N hydrochloric acid
7. 7
   FiltrationThe mixture was filtered
8. 8
   Otherthe layers were separated
9. 9
   Extractionthe aqueous phase was extracted with ethyl acetate
10. 10
    WashThe extract was washed with water
11. 11
    Dryingdried (MgSO4)
12. 12
    Otherevaporated to dryness

Procedure

A suspension of 3.85 g. (0.01 mol.) of 7-amino-3-[1-(2-carbamoylethyl)tetrazol-5-ylthiomethyl]-3-cephem-4-carboxylic acid in 50 ml. of dry dimethylformamide was treated with 2 ml. of triethylamine and the mixture was stirred for 15 minutes at 25°. The activated ester of trifluoromethylmercaptoacetic acid (2.57 g., 0.016 mol.) was added to the mixture and it was stirred an additional hour. The reaction mixture was evaporated to dryness and water and ethyl acetate were added to the residue. The layers were separated, ethyl acetate was added to the aqueous phase and it was acidified to pH 2.5 by addition of 6N hydrochloric acid. The mixture was filtered, the layers were separated and the aqueous phase was extracted with ethyl acetate. The extract was washed with water, dried (MgSO4) and evaporated to dryness to give the title compound.

Source