Réaction #348437

Équation de réaction

2,2,2,-Trichloroethyl 3-bromo-3-methyl-7-(2-phenylacetamido)cepham-4-carboxylate

aniline

→

2,2,2-trichloroethyl 2-anilinomethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylate

Rendement 48.0%

Solvants

methylene chloride

Conditions de réaction

Traitement

1. 1
   Températurecooling
2. 2
   workup.STIRRINGthe mixture was stirred for 4 hours at the same temperature
3. 3
   Filtrationthe reaction mixture was filtered
4. 4
   LavageThe filtrate was washed with a dilute aqueour solution of phosphoric acid
5. 5
   Séchagewith water, dried over magnesium sulfate
6. 6
   Concentrationconcentrated
7. 7
   Lavageeluted with chloroform
8. 8
   AutreThe eluate was separated into fractions of each about 20 ml
9. 9
   Autrethe second to eighth fractions were collected
10. 10
    workup.DISTILLATIONthe solvent was distilled off

Mode opératoire

2,2,2,-Trichloroethyl 3-bromo-3-methyl-7-(2-phenylacetamido)cepham-4-carboxylate (1.10 g) was dissolved in methylene chloride (15 ml) and to this solution was added aniline (0.28 g). And to the solution was added silver fluoroborate (0.45 g) under stirring under ice-cooling and the mixture was stirred for 4 hours at the same temperature. After the reaction was completed, the reaction mixture was filtered. The filtrate was washed with a dilute aqueour solution of phosphoric acid and then with water, dried over magnesium sulfate and concentrated. The residue was subjected to column chromatography on silica gel (25 g) and eluted with chloroform. The eluate was separated into fractions of each about 20 ml and the second to eighth fractions were collected and then the solvent was distilled off to give 2,2,2-trichloroethyl 2-anilinomethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylate (0.54 g), mp 148° to 149° C.

Source