Реакция #348449

Уравнение реакции

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

Растворители

methanol

Условия реакции

Обработка

1. 1
   Температураunder cooling
2. 2
   КонцентрированиеThe reaction mixture was concentrated
3. 3
   workup.DISSOLUTIONthe obtained residue was dissolved in chloroform
4. 4
   ПромывкаThis solution was washed with a saturated sodium bicarbonate aqueous solution and with water
5. 5
   Сушкаdried over magnesium sulfate
6. 6
   ДругоеThe residue obtained
7. 7
   workup.DISTILLATIONby distilling off the solvent
8. 8
   ДругоеThe obtained crystals were recrystallized from carbon tetrachloride

Методика

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.

Источник