Réaction #348433

ord-65c78d0aa7cc49bfa6cfeb9ca324a557

Équation de réaction

COC(=O)C1N2C(=O)C(NC(=O)COc3ccccc3)[C@H]2SC1(C)CBr
methyl 2-bromomethyl-2-methyl-6-(2-phenoxyacetamido)penam-3-carboxylate
Nc1ccccc1
aniline
→
COC(=O)C1N2C(=O)C(NC(=O)COc3ccccc3)[C@H]2SC1(C)CNc1ccccc1
methyl 2-anilinomethyl-2-methyl-6-(2-phenoxyacetamido)-penam-3-carboxylate
Rendement 45.3%

Réactifs

COC(=O)C1N2C(=O)C(NC(=O)COc3ccccc3)[C@H]2SC1(C)CBr
methyl 2-bromomethyl-2-methyl-6-(2-phenoxyacetamido)penam-3-carboxylate
Nc1ccccc1
aniline

Réactifs

F[B-](F)(F)F.[Ag+]
silver fluoroborate

Solvants

ClCCl
methylene chloride

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    workup.ADDITIONBy treating in the similar manner

Mode opératoire

By treating in the similar manner as described in Example 16 using methyl 2-bromomethyl-2-methyl-6-(2-phenoxyacetamido)penam-3-carboxylate (0.88 g), aniline (0.28 g), silver fluoroborate (0.43 g) and methylene chloride (15 ml), there was obtained oily methyl 2-anilinomethyl-2-methyl-6-(2-phenoxyacetamido)-penam-3-carboxylate (0.41 g) from the fractions of the third to seventh.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US04164497uspto-grants-1979_08