Réaction #348451

Équation de réaction

Methyl 2-bromomethyl-2-methyl-6-(2-phenoxyacetamido)penam- 3-carboxylate

methanol

→

Methyl 3-methoxy-3-methyl-7-(2-phenoxyacetamido)cepham- 4-carboxylate

Solvants

methylene chloride

Conditions de réaction

Traitement

1. 1
   AutreAfter the reaction
2. 2
   Filtrationthe reaction mixture was filtered
3. 3
   Lavagethe filtrate was washed with a dilute sodium bicarbonate aqueous solution
4. 4
   SéchageThe solution was dried over magnesium sulfate
5. 5
   Concentrationconcentrated
6. 6
   Lavageeluted with chloroform
7. 7
   AutreThe elute was separated into fractions of each about 20 ml
8. 8
   Autrethe seventh to tenth fractions were collected
9. 9
   workup.DISTILLATIONThe solvent was distilled off

Mode opératoire

Methyl 2-bromomethyl-2-methyl-6-(2-phenoxyacetamido)penam- 3-carboxylate (0.88 g) was dissolved in methylene chloride (13 ml) containing methanol. To the solution was added silver fluoroborate (0.45 g), and the mixture was stirred for 2 hours. After the reaction, the reaction mixture was filtered and the filtrate was washed with a dilute sodium bicarbonate aqueous solution and then with water. The solution was dried over magnesium sulfate and concentrated. The residue was subjected to column chromatography on silica gel (25 g) and eluted with chloroform. The elute was separated into fractions of each about 20 ml and the seventh to tenth fractions were collected. The solvent was distilled off to give Methyl 3-methoxy-3-methyl-7-(2-phenoxyacetamido)cepham- 4-carboxylate (0.60 g).

Source