Methanol → HCID 70590175, compound

HRID 1438797Notes

Reaction equation

HRID 1438797 reaction equation
Br[CH2:2][C:3]1([CH3:26])[CH:7]([C:8]([O:10][CH3:11])=[O:9])[N:6]2[C:12](=[O:25])[CH:13]([NH:14][C:15](=[O:24])[CH2:16][O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C@H:5]2[S:4]1.[CH3:27][OH:28]>C(Cl)Cl.F[B-](F)(F)F.[Ag+]>[CH3:27][O:28][C:3]1([CH3:26])[CH:7]([C:8]([O:10][CH3:11])=[O:9])[N:6]2[C:12](=[O:25])[CH:13]([NH:14][C:15](=[O:24])[CH2:16][O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C@H:5]2[S:4][CH2:2]1

Participants

5

Reactant 2

HCID 887MethanolHCID 70360981HCID 70360981, compound

Product 1

HCID 70590175HCID 70590175, compound

Reagents, catalysts & solvents 2

HCID 159722Silver tetrafluoroborateCatalystHCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  1. customAfter the reaction
  2. filtrationthe reaction mixture was filtered
  3. washthe filtrate was washed with a dilute sodium bicarbonate aqueous solution
  4. dry with materialThe solution was dried over magnesium sulfate
  5. concentrationconcentrated
  6. washeluted with chloroform
  7. customThe elute was separated into fractions of each about 20 ml
  8. customthe seventh to tenth fractions were collected
  9. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-dc2a59549df84596b392c5fe77867a97
Source dataset
uspto-grants-1977_11
Patent number
US04056521

Reaction notes

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