Acetic Acid → HCID 86733384, compound

HRID 1856178Notes

Reaction equation

HRID 1856178 reaction equation
[C:1](O)(=O)[CH3:2].[N:5]1([C:11]([S:13][CH2:14][C:15]2([CH3:41])[CH:19]([C:20]([O:22]CC(Cl)(Cl)Cl)=[O:21])[N:18]3[C:28](=[O:40])[CH:29]([NH:30][C:31](=[O:39])[CH2:32][C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[C@H:17]3[S:16]2)=[S:12])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1>CN(C)C=O.[Zn]>[N:5]1([C:11]([S:13][CH2:14][C:15]2([CH3:41])[CH:19]([C:20]([OH:22])=[O:21])[N:18]3[C:28](=[O:40])[CH:29]([NH:30][C:31](=[O:39])[CH2:32][C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=4)[C@H:17]3[S:16]2)=[S:12])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1.[CH2:32]([NH:30][CH2:29][CH2:17][NH:18][CH2:19][C:1]1[CH:2]=[CH:9][CH:8]=[CH:7][CH:6]=1)[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 86733386HCID 86733386, compound

Product 1

HCID 86733384HCID 86733384, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 6228DimethylformamideSolvent

Procedure

Acetic acid (1 ml) and zinc powder (0.80 g) were added to a solution of 2,2,2-trichloroethyl 2-piperidinothiocarbonylthiomethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylate (0.95 g) in dimethylformamide (5 ml) under ice-cooling and the mixture was stirred for 1 hour and 40 minutes. After the reaction, zinc powder was filtered off and the filtrate was poured into ethyl acetate. The solution was washed with 3% hydrochloric acid and then with water (four times) and dried over magnesium sulfate. After drying, the solvent was distilled off and the residue was dissolved in a small amount of methanol. To this solution was added an aqueous solution of N,N'-dibenzylethylenediamine diacetate and precipitates were collected by filtration, washed with water to give N,N'-dibenzylethylenediamine 2-piperidinothiocarbonylthiomethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylate (0.30 g), mp. 100° C. (dec.)

Workup

  1. temperaturecooling
  2. filtrationwas filtered off
  3. additionthe filtrate was poured into ethyl acetate
  4. washThe solution was washed with 3% hydrochloric acid
  5. dry with materialwith water (four times) and dried over magnesium sulfate
  6. customAfter drying
  7. distillationthe solvent was distilled off
  8. dissolutionthe residue was dissolved in a small amount of methanol
  9. additionTo this solution was added an aqueous solution of N,N'-dibenzylethylenediamine diacetate
  10. customprecipitates
  11. filtrationwere collected by filtration
  12. washwashed with water

Sources & evidence

ORD record
ord-80e2d12d8d6c44fba18d777d66d33b1e
Source dataset
uspto-grants-1980_08
Patent number
US04218374

Reaction notes

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