Acetic Acid → HCID 70591997, compound

HRID 261262Notes

Reaction equation

HRID 261262 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 extracted 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. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. customdried
  6. distillationthe solvent was distilled off
  7. dissolutionThe residue was dissolved in methanol (0.8 ml) and to this solution
  8. additionwas added a solution of N,N'-dibenzylethylenediamine diacetate (0.18 g) in water (5 ml)
  9. customprecipitates
  10. filtrationwere collected by filtration
  11. washwashed with water
  12. customdried

Sources & evidence

ORD record
ord-272c5f9c5878411e9f07098046454355
Source dataset
uspto-grants-1979_08
Patent number
US04164497

Reaction notes

Loading…