Isopropanol → HCID 70590458, compound

HRID 261268Notes

Reaction equation

HRID 261268 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.[CH:30]([OH:33])([CH3:32])[CH3:31]>O1CCCC1.F[B-](F)(F)F.[Ag+]>[CH3:29][C:3]1([O:33][CH:30]([CH3:32])[CH3:31])[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:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[C@H:5]2[S:4][CH2:2]1

Participants

5

Reactant 2

HCID 3776IsopropanolHCID 128952622,2,2-Trichloroethyl 2-bromomethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylate

Product 1

HCID 70590458HCID 70590458, compound

Reagents, catalysts & solvents 2

HCID 159722Silver tetrafluoroborateCatalystHCID 8028TetrahydrofuranSolvent

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 isopropanol (5 ml). To this solution was added silver fluoroborate (0.24 g) under ice-cooling and 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 then dried over magnesium sulfate. The residue obtained by distilling off the solvent was purified by chromatography on silica gel using chloroform as developing solvent to give oily 2,2,2-trichloroethyl 3-methyl-3-isopropoxy-7-(2-phenylacetamido)-cepham-4-carboxylate (0.10 g).

Workup

  1. temperaturecooling
  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. customwas purified by chromatography on silica gel

Sources & evidence

ORD record
ord-9f9cc1f56d324d79a86f950414cccacc
Source dataset
uspto-grants-1979_08
Patent number
US04164497

Reaction notes

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