2,2,2-Trichloroethyl 2-methyl-2,3-methylene-6-(2-phenylacetamido)penam-3-carboxylate → 2-Methyl-2,3-methylene-6-(2-phenylacetamido)penam-3-carboxylic acid

HRID 1287326Notes

Reaction equation

HRID 1287326 reaction equation
[CH3:1][C:2]12[CH2:15][C:6]1([C:7]([O:9]CC(Cl)(Cl)Cl)=[O:8])[N:5]1[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:4]1[S:3]2>CN(C)C=O.C(O)(=O)C.[Zn]>[CH3:1][C:2]12[CH2:15][C:6]1([C:7]([OH:9])=[O:8])[N:5]1[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:4]1[S:3]2

Participants

5

Reactant 1

HCID 128339582,2,2-Trichloroethyl 2-methyl-2,3-methylene-6-(2-phenylacetamido)penam-3-carboxylate

Product 1

HCID 705294222-Methyl-2,3-methylene-6-(2-phenylacetamido)penam-3-carboxylic acidYield 83.7%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalyst2×HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,2,2-trichloroethyl 2-methyl-2,3-methylene-6-(2-phenylacetamido)penam-3-carboxylate (517 mg.) in a mixture of dimethylformamide (3 ml.) and acetic acid (1 ml.) was added zinc powder (0.7 g.) under ice-cooling. After stirring for 1 hour at the same temperature, zinc powder was filtered off and washed twice with dimethylformamide (2 ml.). The filtrate was combined with the washings and the combined solution was poured into a mixed cooled solution of ethyl acetate and water, extracted with ethyl acetate, after which the extract was washed with water and dried over magnesium sulfate. Crystalline material (390 mg.) obtained by distilling off the solvent under reduced pressure was washed with ether and dried to give colorless crystals of 2-methyl-2,3-methylene-6-(2-phenylacetamido)penam-3-carboxylic acid (310 mg.) mp 112° to 118°C (dec.).

Workup

  1. temperaturecooling
  2. filtrationwas filtered off
  3. washwashed twice with dimethylformamide (2 ml.)
  4. additionthe combined solution was poured into a mixed
  5. temperaturecooled solution of ethyl acetate and water
  6. extractionextracted with ethyl acetate
  7. washafter which the extract was washed with water
  8. dry with materialdried over magnesium sulfate
  9. customCrystalline material (390 mg.) obtained
  10. distillationby distilling off the solvent under reduced pressure
  11. washwas washed with ether
  12. customdried

Sources & evidence

ORD record
ord-15a12ed328bc46588606fa17d5b10e2d
Source dataset
uspto-grants-1976_10
Patent number
US03984397

Reaction notes

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