Acetic Acid → HCID 131711256, compound

HRID 1764032Notes

Reaction equation

HRID 1764032 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:23])[CH:17]([NH:18][C:19](=[S:22])[CH2:20][CH3:21])[C@H:4]2[S:3]1.C(O)(=O)C>[Zn].CN(C)C=O>[CH3:1][CH:2]1[CH:7]=[C:6]([C:8]([OH:10])=[O:9])[N:5]2[C:16](=[O:23])[CH:17]([NH:18][C:19](=[S:22])[CH2:20][CH3:21])[C@H:4]2[S:3]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 131711257HCID 131711257, compound

Product 1

HCID 131711256HCID 131711256, compoundYield 88.1%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 6228DimethylformamideSolvent

Procedure

2,2,2-Trichloroethyl 2-methyl-7-(2-methylthioacetamido)-3-cephem-4-carboxylate (0.48 g), glacial acetic acid (0.48 ml) and zinc powder (0.48 g) were added to anhydrous dimethylformamide (5 ml), and the mixture was stirred for 1 hour under ice-cooling. After the reaction, zinc powder was filtered off. The filtrate was poured into a mixture of 3% hydrochloric acid (10 ml) and ethyl acetate (10 ml), and the ethyl acetate layer was separated. The aqueous layer was further extracted three times with ethyl acetate (10 ml). The ethyl acetate layer was combined. The combined extract was washed with a saturated sodium chloride aqueous solution and dried over magnesium sulfate, after which the solvent was distilled off under reduced pressure. The obtained residue was crystallized by adding ether and the crystals were collected by filtration and washed with ether to give 2-methyl-7-(2-methylthioacetamido)-3-cephem-4-carboxylic acid (0.29 g), mp 181° to 183° C. (dec.).

Workup

  1. temperaturecooling
  2. filtrationwas filtered off
  3. additionThe filtrate was poured into a mixture of 3% hydrochloric acid (10 ml) and ethyl acetate (10 ml)
  4. customthe ethyl acetate layer was separated
  5. extractionThe aqueous layer was further extracted three times with ethyl acetate (10 ml)
  6. extractionThe combined extract
  7. washwas washed with a saturated sodium chloride aqueous solution
  8. dry with materialdried over magnesium sulfate
  9. distillationafter which the solvent was distilled off under reduced pressure
  10. customThe obtained residue was crystallized
  11. additionby adding ether
  12. filtrationthe crystals were collected by filtration
  13. washwashed with ether

Sources & evidence

ORD record
ord-9d708d54d85943aeb646f88bb14f317a
Source dataset
uspto-grants-1978_09
Patent number
US04113940

Reaction notes

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