Tetrahydrofuran → 2,2,2-Trichloroethyl 3-methyl-3-methoxy-7-(2-phenylacetamido)-cepham-4-carboxylate

HRID 261267Notes

Reaction equation

HRID 261267 reaction equation
Br[CH2:2][C:3]1([CH3:29])[CH:7]([C:8]([O:10][CH2:11][C:12]([Cl:15])([Cl:14])[Cl:13])=[O:9])[N:6]2[C:16](=[O:28])[CH:17]([NH:18][C:19](=[O:27])[CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C@H:5]2[S:4]1.[O:30]1CCC[CH2:31]1>CO.F[B-](F)(F)F.[Ag+]>[CH3:2][C:3]1([O:30][CH3:31])[CH:7]([C:8]([O:10][CH2:11][C:12]([Cl:14])([Cl:15])[Cl:13])=[O:9])[N:6]2[C:16](=[O:28])[CH:17]([NH:18][C:19](=[O:27])[CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C@H:5]2[S:4][CH2:29]1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 128952622,2,2-Trichloroethyl 2-bromomethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylate

Product 1

HCID 705907752,2,2-Trichloroethyl 3-methyl-3-methoxy-7-(2-phenylacetamido)-cepham-4-carboxylate

Reagents, catalysts & solvents 2

HCID 159722Silver tetrafluoroborateCatalystHCID 887MethanolSolvent

Procedure

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.

Workup

  1. temperatureunder cooling
  2. concentrationThe reaction mixture was concentrated
  3. dissolutionthe obtained residue was dissolved in chloroform
  4. washThis solution was washed with a saturated sodium bicarbonate aqueous solution and with water
  5. dry with materialdried over magnesium sulfate
  6. customThe residue obtained
  7. distillationby distilling off the solvent
  8. customThe obtained crystals were recrystallized from carbon tetrachloride

Sources & evidence

ORD record
ord-e5bc4544423c472f9866af680671b52c
Source dataset
uspto-grants-1979_08
Patent number
US04164497

Reaction notes

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