Réaction #348449

Équation de réaction

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

tetrahydrofuran

→

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

Solvants

methanol

Conditions de réaction

Traitement

1. 1
   Températureunder cooling
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
   AutreThe obtained crystals were recrystallized from carbon tetrachloride

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 methanol (5 ml). To this solution was added silver fluoroborate (0.24 g) under cooling and then 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 dried over magnesium sulfate. The residue obtained by distilling off the solvent was subjected to chromatography on silica gel using chloroform as developing solvent. The obtained crystals were recrystallized from carbon tetrachloride to give 2,2,2-trichloroethyl 3-methyl-3-methoxy-7-(2-phenylacetamido)-cepham-4-carboxylate (0.27 g), mp. 132° to 133° C.

Source