Acetic Acid → HCID 131711258, compound

HRID 1660622Notes

Reaction equation

HRID 1660622 reaction equation
[CH3:1][CH:2]1[CH:7]=[C:6]([C:8]([O:10]CC(Cl)(Cl)Cl)=[O:9])[N:5]2[C:16](=[O:25])[CH:17]([NH:18][C:19](=[S:24])[CH2:20][CH2:21][CH:22]=[CH2:23])[C@H:4]2[S:3]1.C(O)(=O)C>CN(C)C=O.[Zn]>[CH3:1][CH:2]1[CH:7]=[C:6]([C:8]([OH:10])=[O:9])[N:5]2[C:16](=[O:25])[CH:17]([NH:18][C:19](=[S:24])[CH2:20][CH2:21][CH:22]=[CH2:23])[C@H:4]2[S:3]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 131711253HCID 131711253, compound

Product 1

HCID 131711258HCID 131711258, compoundYield 94.4%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 6228DimethylformamideSolvent

Procedure

Zinc powder (5.55 g) was added to a solution of 2,2,2-trichloroethyl 2-methyl-7-(2-allylthioacetamido)-3-cephem-4-carboxylate (5.55 g) in anhydrous dimethylformamide (55.5 ml) and then acetic acid (5.5 ml) was dropwise added to the solution, after which the mixture was stirred for 1 hour. After the reaction, zinc powder was filtered off and washed with ethyl acetate. The filtrate and the washings were combined, after which the solution was poured into a mixture of 5% hydrochloric acid (250 ml) and ethyl acetate (100 ml), and then extracted. The aqueous layer was further extracted twice with ethyl acetate. The ethyl acetate layer was combined, and the combined ethyl acetate layer was washed with a saturated sodium chloride aqueous solution, and then dried over magnesium sulfate. After the solution was concentrated under reduced pressure till the volume of the solution becomes about 40 ml. Crystals precipitated were collected by filtration and washed with isopropyl ether and dried to give colorless crystals of 2-methyl-7-(2-allylthioacetamido)-3-cephem-4-carboxylic acid (3.69 g), mp 121° to 123° C. Moreover the filtrate was concentrated and the obtained crystals were washed with isopropyl ether and then dried to give 2-methyl-7-(2-allylthioacetamido)-3-cephem-4-carboxylic acid (0.75 g).

Workup

  1. filtrationwas filtered off
  2. washwashed with ethyl acetate
  3. additionafter which the solution was poured into a mixture of 5% hydrochloric acid (250 ml) and ethyl acetate (100 ml)
  4. extractionextracted
  5. extractionThe aqueous layer was further extracted twice with ethyl acetate
  6. washthe combined ethyl acetate layer was washed with a saturated sodium chloride aqueous solution
  7. dry with materialdried over magnesium sulfate
  8. concentrationAfter the solution was concentrated under reduced pressure till the volume of the solution
  9. customCrystals precipitated
  10. filtrationwere collected by filtration
  11. washwashed with isopropyl ether
  12. customdried

Sources & evidence

ORD record
ord-4e2749e0abf44e739282c64f35f8f2ca
Source dataset
uspto-grants-1981_12
Patent number
US04308380

Reaction notes

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