HCID 88834605, compound → HCID 88834203, compound

HRID 1287333Notes

Reaction equation

HRID 1287333 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:28])[CH:17]([NH:18][C:19]([S:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:20])[C@H:4]1[S:3]2>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:28])[CH:17]([NH:18][C:19]([S:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:20])[C@H:4]1[S:3]2

Participants

5

Reactant 1

HCID 88834605HCID 88834605, compound

Product 1

HCID 88834203HCID 88834203, compoundYield 56.8%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalyst2×HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,2,2-trichloroethyl 2-methyl-2,3-methylene-6-(phenylthio)carbonylaminopenam-3-carboxylate (1.04 g.) in a mixture of dimethylformamide (7 ml.) and acetic acid (2.2 ml.) was added zinc powder (1.8 g.) under ice-cooling, and the mixture was stirred for 1.5 hours. After the reaction, zinc powder was filtered off and the filtrate was poured into a mixture of ethyl acetate (30 ml.) and ice-water (30 ml.) containing 2% hydrochloric acid (2 ml.), extracted and then the aqueous layer was further extracted with ethyl acetate (10 ml.) The combined extract was washed with water and a saturated sodium chloride aqueous solution in turn, dried over magnesium sulfate and then the solvent was removed under reduced pressure. The obtained residue was crystallized by adding a small amount of acetonitrile to give 2-methyl-2,3-methylene-6-(phenylthio)carbonylaminopenam-3-carboxylic acid (0.43 g.), mp 116° to 119°C (dec.).

Workup

  1. temperaturecooling
  2. filtrationwas filtered off
  3. additionthe filtrate was poured into a mixture of ethyl acetate (30 ml.) and ice-water (30 ml.)
  4. additioncontaining 2% hydrochloric acid (2 ml.)
  5. extractionextracted
  6. extractionthe aqueous layer was further extracted with ethyl acetate (10 ml.) The
  7. extractioncombined extract
  8. washwas washed with water
  9. dry with materiala saturated sodium chloride aqueous solution in turn, dried over magnesium sulfate
  10. customthe solvent was removed under reduced pressure
  11. customThe obtained residue was crystallized
  12. additionby adding a small amount of acetonitrile

Sources & evidence

ORD record
ord-6057a6cb9a004c07936c01704961bd17
Source dataset
uspto-grants-1976_10
Patent number
US03984397

Reaction notes

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