Hydrochloric Acid → HCID 15582366, compound

HRID 1287327Notes

Reaction equation

HRID 1287327 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:27])[CH:17]([NH:18][C:19](=[O:26])[CH2:20][N:21]3[CH:25]=[N:24][N:23]=[N:22]3)[C@H:4]1[S:3]2.Cl.[Cl-].[Na+].C(OCC)(=O)C>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:27])[CH:17]([NH:18][C:19](=[O:26])[CH2:20][N:21]3[CH:25]=[N:24][N:23]=[N:22]3)[C@H:4]1[S:3]2

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 8857Ethyl AcetateHCID 15582369HCID 15582369, compound

Product 1

HCID 15582366HCID 15582366, compoundYield 69.5%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,2,2-trichloroethyl 2-methyl-2,3-methylene-6-[2-(1H-tetrazol-1-yl)acetamido]penam-3-carboxylate (0.91 g.) in a mixture of dimethylformamide (5 ml.) and acetic acid (1.5 ml.) was added zinc powder (1.2 g.) under ice-cooling, and the mixture was stirred for 1 hour. After the reaction, the reaction mixture was poured into a mixture of 2% hydrochloric acid saturated with sodium chloride (30 ml.) and ethyl acetate (50 ml.), extracted and the aqueous layer was further extracted with ethyl acetate (10 ml.). The combined ethyl acetate layer was washed with a saturated sodium chloride aqueous solution and dried over magnesium sulfate. After drying, residue obtained by distilling off the solvent under reduced pressure was crystallized by adding a small amount of ethyl acetate and the crystals were collected by filtration to give 2-methyl-2,3-methylene-6-[2-(1H-tetrazol-1-yl)acetamido]penam-3-carboxylic acid (0.45 g.), mp 167° to 170°C (dec.).

Workup

  1. temperaturecooling
  2. customAfter the reaction
  3. extractionextracted
  4. extractionthe aqueous layer was further extracted with ethyl acetate (10 ml.)
  5. washThe combined ethyl acetate layer was washed with a saturated sodium chloride aqueous solution
  6. dry with materialdried over magnesium sulfate
  7. customAfter drying
  8. customresidue obtained
  9. distillationby distilling off the solvent under reduced pressure
  10. customwas crystallized
  11. additionby adding a small amount of ethyl acetate
  12. filtrationthe crystals were collected by filtration

Sources & evidence

ORD record
ord-e739e6057b4d494dbb757b1a882a437b
Source dataset
uspto-grants-1976_10
Patent number
US03984397

Reaction notes

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