Acetic Acid → 2-Methyl-7-amino-3-cephem-4-carboxylic acid

HRID 1764035Notes

Reaction equation

HRID 1764035 reaction equation
C(O)(=O)C.Cl.[CH3:6][CH:7]1[CH:12]=[C:11]([C:13]([O:15]CC(Cl)(Cl)Cl)=[O:14])[N:10]2[C:21](=[O:24])[CH:22]([NH2:23])[C@H:9]2[S:8]1>CN(C)C=O.[Zn]>[CH3:6][CH:7]1[CH:12]=[C:11]([C:13]([OH:15])=[O:14])[N:10]2[C:21](=[O:24])[CH:22]([NH2:23])[C@H:9]2[S:8]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 128341352,2,2-Trichloroethyl 2-methyl-7-amino-3-cephem-4-carboxylate hydrochloride

Product 1

HCID 128022512-Methyl-7-amino-3-cephem-4-carboxylic acidYield 44.3%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6228DimethylformamideSolvent

Procedure

Acetic acid (1 ml) and zinc powder (2.0 g) were added under ice-cooling to a solution of 2,2,2-trichloroethyl 2-methyl-7-amino-3-cephem-4-carboxylate hydrochloride (1.53 g) in dimethylformamide (10 ml) and the mixture was stirred for 1 hour at -5° to 0° C., after which the reaction mixture was filtered. The filtered zinc powder was washed with dimethylformamide and the filtrate and the washings were combined, after which a few mls. of water was added to the solution. The precipitated crystals were collected by filtration and dissolved in a small amount of a sodium bicarbonate aqueous solution and then the insoluble material was filtered off. The filtrate was adjusted to pH4 with 10% hydrochloric acid and the precipitated crystals were collected by filtration, washed with water and acetone and dried to give 2-methyl-7-amino-3-cephem-4-carboxylic acid (0.38 g), mp 222° C. (dec.).

Workup

  1. filtrationafter which the reaction mixture was filtered
  2. washThe filtered zinc powder was washed with dimethylformamide
  3. additionof water was added to the solution
  4. filtrationThe precipitated crystals were collected by filtration
  5. dissolutiondissolved in a small amount of a sodium bicarbonate aqueous solution
  6. filtrationthe insoluble material was filtered off
  7. filtrationthe precipitated crystals were collected by filtration
  8. washwashed with water and acetone
  9. customdried

Sources & evidence

ORD record
ord-97e3efa20a684a09a32061061c85833e
Source dataset
uspto-grants-1978_09
Patent number
US04113940

Reaction notes

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