Réaction #348450

Équation de réaction

2,2,2-Trichloroethyl 2-bromomethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylate

isopropanol

→

2,2,2-trichloroethyl 3-methyl-3-isopropoxy-7-(2-phenylacetamido)-cepham-4-carboxylate

Solvants

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   Températurecooling
2. 2
   ConcentrationThe reaction mixture was concentrated
3. 3
   workup.DISSOLUTIONthe obtained residue was dissolved in chloroform
4. 4
   LavageThis solution was washed with a saturated sodium bicarbonate aqueous solution and with water
5. 5
   Séchagedried over magnesium sulfate
6. 6
   AutreThe residue obtained
7. 7
   workup.DISTILLATIONby distilling off the solvent
8. 8
   Autrewas purified by chromatography on silica gel

Mode opératoire

2,2,2-Trichloroethyl 2-bromomethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylate (0.55 g) was dissolved in a mixture of tetrahydrofuran (5 ml) and isopropanol (5 ml). To this solution was added silver fluoroborate (0.24 g) under ice-cooling and the mixture was stirred for 1 hour. The reaction mixture was concentrated and the obtained residue was dissolved in chloroform. This solution was washed with a saturated sodium bicarbonate aqueous solution and with water and then dried over magnesium sulfate. The residue obtained by distilling off the solvent was purified by chromatography on silica gel using chloroform as developing solvent to give oily 2,2,2-trichloroethyl 3-methyl-3-isopropoxy-7-(2-phenylacetamido)-cepham-4-carboxylate (0.10 g).

Source