Acetic Acid → HCID 70591997, compound

HRID 2083159Notes

Reaction equation

HRID 2083159 reaction equation
[CH3:1][N:2]1[C:6]([S:7][CH2:8][C:9]2([CH3:41])[CH:13]([C:14]([O:16]CC(Cl)(Cl)Cl)=[O:15])[N:12]3[C:22](=[O:40])[CH:23]([NH:24][C:25]([C:27]4[C:28]([C:33]5[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=5[Cl:39])=[N:29][O:30][C:31]=4[CH3:32])=[O:26])[C@H:11]3[S:10]2)=[N:5][N:4]=[N:3]1.[C:42](O)(=O)[CH3:43]>CN(C)C=O.[Zn]>[CH3:1][N:2]1[C:6]([S:7][CH2:8][C:9]2([CH3:41])[CH:13]([C:14]([OH:16])=[O:15])[N:12]3[C:22](=[O:40])[CH:23]([NH:24][C:25]([C:27]4[C:28]([C:33]5[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=5[Cl:39])=[N:29][O:30][C:31]=4[CH3:32])=[O:26])[C@H:11]3[S:10]2)=[N:5][N:4]=[N:3]1.[CH2:28]([NH:29][CH2:42][CH2:43][NH:29][CH2:28][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 70590563HCID 70590563, compound

Product 1

HCID 70591997HCID 70591997, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
-15 °C

Procedure

2,2,2-Trichloroethyl 2-(1-methyl-1H-tetrazol-5-yl)thiomethyl-2-methyl-6-[3-(2-chlorophenyl)-5-methylisoxazole-4-carboxamido]penam-3-carboxylate (0.67 g) was dissolved in dimethylformamide (5 ml). To this solution were added acetic acid (0.8 ml) and zinc powder (0.7 g) under cooling at -15° C and the mixture was stirred for 2 hours at the same temperature. After the reaction, zinc powder was filtered off and the filtrate was poured into 5% hydrochloric acid (20 ml) and then extraxted with ethyl acetate. The extract was washed with water, dried and the solvent was distilled off. The residue was dissolved in methanol (0.8 ml) and to this solution was added a solution of N,N'-dibenzylethylenediamine diacetate (0.18 g) in water (5 ml) and precipitates were collected by filtration, washed with water and dried to give N,N'-dibenzylethylenediamine 2-(1-methyl-1H-tetrazol-5-yl)thiomethyl-2-methyl-6-[3-(2-chlorophenyl)-5-methylisoxazole-4-carboxamido]penam-3-carboxylate (0.24 g), mp. 117° to 119° C (dec.).

Workup

  1. filtrationwas filtered off
  2. additionthe filtrate was poured into 5% hydrochloric acid (20 ml)
  3. washThe extract was washed with water
  4. customdried
  5. distillationthe solvent was distilled off
  6. dissolutionThe residue was dissolved in methanol (0.8 ml) and to this solution
  7. additionwas added a solution of N,N'-dibenzylethylenediamine diacetate (0.18 g) in water (5 ml)
  8. customprecipitates
  9. filtrationwere collected by filtration
  10. washwashed with water
  11. customdried

Sources & evidence

ORD record
ord-3f7d412fe89844f0a0d0fa257604fa93
Source dataset
uspto-grants-1978_04
Patent number
US04084049

Reaction notes

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