Methanol → 2,2,2-Trichloroethyl 2-methoxymethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylate

HRID 1075984Notes

Reaction equation

HRID 1075984 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.[CH3:30][OH:31]>C(Cl)Cl.F[B-](F)(F)F.[Ag+]>[CH3:30][O:31][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

Participants

5

Reactant 2

HCID 887MethanolHCID 128952622,2,2-Trichloroethyl 2-bromomethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylate

Product 1

HCID 705904432,2,2-Trichloroethyl 2-methoxymethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylate

Reagents, catalysts & solvents 2

HCID 159722Silver tetrafluoroborateCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

2,2,2-Trichloroethyl 2-bromomethyl-2-methyl-6-(2-phenylacetamido)-penam-3-carboxylate (1.10 g) was dissolved in methylene chloride (12 ml) and to this solution was added methanol (3 ml). And to the solution was added silver fluoroborate (0.45 g) under stirring under cooling at -10°C and the mixture was stirred for 2 hours at the same temperature. After the reaction was completed, the reaction mixture was filtered and the filtrate was washed with sodium bicarbonate aqueous solution and then with water, dried over magnesium sulfate and thereafter concentrated. The residue was subjected to column chromatography on silica gel (25 g) and eluted with chloroform. The eluate was separated into fractions of about 20 ml and the first and second fractions were collected. After distilling off the solvent, the residue was dried to give oily 2,2,2-trichloroethyl 2-methoxymethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylate. Infrared Absorption Spectrum (CHCl3) 3360, 1785, 1757, 1666 cm-1.

Workup

  1. stirringthe mixture was stirred for 2 hours at the same temperature
  2. filtrationthe reaction mixture was filtered
  3. washthe filtrate was washed with sodium bicarbonate aqueous solution
  4. dry with materialwith water, dried over magnesium sulfate
  5. concentrationconcentrated
  6. washeluted with chloroform
  7. customThe eluate was separated into fractions of about 20 ml
  8. customthe first and second fractions were collected
  9. distillationAfter distilling off the solvent
  10. customthe residue was dried

Sources & evidence

ORD record
ord-efca60eab76247f699bac04f31c6e52c
Source dataset
uspto-grants-1976_05
Patent number
US03954732

Reaction notes

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