Acetic Acid → HCID 131710475, compound

HRID 1287332Notes

Reaction equation

HRID 1287332 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:33])[CH:17]([NH:18][C:19](=[O:32])[C:20](=[N:27][NH:28][C:29](=[O:31])[NH2:30])[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C@H:4]1[S:3]2.C(O)(=O)C>CN(C)C=O.[Zn]>[CH3:1][C:2]12[CH2:15][C:6]1([C:7]([OH:9])=[O:8])[N:5]1[C:16](=[O:33])[CH:17]([NH:18][C:19](=[O:32])[C:20](=[N:27][NH:28][C:29](=[O:31])[NH2:30])[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C@H:4]1[S:3]2

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 131710476HCID 131710476, compound

Product 1

HCID 131710475HCID 131710475, compoundYield 63.9%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,2,2-trichloroethyl 2-methyl-2,3-methylene-6-(2-phenyl-2-carbamoylhydrazonoacetamido)penam-3-carboxylate (560 mg.) in dimethylformamide (3 ml.) were added acetic acid (0.8 ml.) and zinc powder (0.75 g.) under ice-cooling, and the mixture was stirred for 1.5 hours. Zinc powder was filtered off, washed with dimethylformamide and the filtrate and the washings were combined, after which the combined solution was poured into ice-water. The solution was adjusted to pH 2 with 10% hydrochloric acid and precipitated crystals were filtered, washed with ethyl acetate and dissolved in a sodium bicarbonated aqueous solution. Insoluble material was filtered off and the filtrate was acidified with 10% hydrochloric acid to give 2-methyl-2,3-methylene-6-(2-phenyl-2-carbamoylhydrazonoacetamido)penam-3-carboxylic acid (270 mg.), mp 198° to 199°C (dec.).

Workup

  1. temperaturecooling
  2. filtrationZinc powder was filtered off
  3. washwashed with dimethylformamide
  4. additionafter which the combined solution was poured into ice-water
  5. customprecipitated crystals
  6. filtrationwere filtered
  7. washwashed with ethyl acetate
  8. dissolutiondissolved in a sodium bicarbonated aqueous solution
  9. filtrationInsoluble material was filtered off

Sources & evidence

ORD record
ord-544e3b0b21b14ca29c940a8355647a91
Source dataset
uspto-grants-1976_10
Patent number
US03984397

Reaction notes

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