Acetic Acid → 2,2,2-Trichloroethyl 2-acetoxymethyl-2-methyl-6-(2-phenylacetamido)-penam-3-carboxylate

HRID 261249Notes

Reaction equation

HRID 261249 reaction equation
[C:1]([OH:4])(=[O:3])[CH3:2].Br[CH2:6][C:7]1([CH3:33])[CH:11]([C:12]([O:14][CH2:15][C:16]([Cl:19])([Cl:18])[Cl:17])=[O:13])[N:10]2[C:20](=[O:32])[CH:21]([NH:22][C:23](=[O:31])[CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C@H:9]2[S:8]1>C(Cl)Cl.C([O-])(=O)C.[Ag+]>[C:1]([O:4][CH2:6][C:7]1([CH3:33])[CH:11]([C:12]([O:14][CH2:15][C:16]([Cl:17])([Cl:18])[Cl:19])=[O:13])[N:10]2[C:20](=[O:32])[CH:21]([NH:22][C:23](=[O:31])[CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C@H:9]2[S:8]1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 128952622,2,2-Trichloroethyl 2-bromomethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylate

Product 1

HCID 705904892,2,2-Trichloroethyl 2-acetoxymethyl-2-methyl-6-(2-phenylacetamido)-penam-3-carboxylate

Reagents, catalysts & solvents 2

HCID 11246Silver acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

Acetic acid (2 ml) was added to a solution of 2,2,2-trichloroethyl 2-bromomethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylate (0.54 g) in methylene chloride (10 ml). And to this solution was added silver acetate (0.34 g) under stirring at room temperature and then the mixture was stirred for 2.5 hours. After the reaction was completed, the reaction mixture was filtered under reduced pressure and the filtrate was washed with 5% hydrochloric acid and then filtered again. The oily residue was crystallized by treating with ether and the crystals were collected by filtration and then dried to give colorless needles of 2,2,2-trichloroethyl 2-acetoxymethyl-2-methyl-6-(2-phenylacetamido)-penam-3-carboxylate (0.21 g), mp 116° to 118° C.

Workup

  1. stirringthe mixture was stirred for 2.5 hours
  2. filtrationthe reaction mixture was filtered under reduced pressure
  3. washthe filtrate was washed with 5% hydrochloric acid
  4. filtrationfiltered again
  5. customThe oily residue was crystallized
  6. additionby treating with ether
  7. filtrationthe crystals were collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-e33c335ace4741128344b58a84cdee6b
Source dataset
uspto-grants-1979_08
Patent number
US04164497

Reaction notes

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