Dimethylformamide → HCID 12833972, compound

HRID 1660613Notes

Reaction equation

HRID 1660613 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: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]2[S:3]1.CN(C)C=O>[Zn].C(O)(=O)C>[CH3:1][CH:2]1[CH:7]=[C:6]([C:8]([OH:10])=[O:9])[N:5]2[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]2[S:3]1

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 12833969HCID 12833969, compound

Product 1

HCID 12833972HCID 12833972, compoundYield 68.1%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 176Acetic AcidSolvent

Procedure

Zinc powder (2.4 g) was added under ice-cooling and stirring to a solution of 2,2,2-trichloroethyl 2-methyl-7-[2-(1H-tetrazol-1-yl)acetamido]-3-cephem-4-carboxylate (2.0 g) in a mixture of anhydrous dimethylformamide (10 ml) and acetic acid (3 ml), and the mixture was stirred for 1.5 hours at the same temperature. After the reaction, zinc powder was filtered off, and the filtrate was extracted by pouring into a matrix of ethyl acetate (50 ml), ice-water and 10% hydrochloric acid (5 ml). The aqueous layer was further extracted with ethyl acetate (10 ml) and the ethyl acetate extract was combined, washed twice with water and dried over magnesium sulfate. After the solvent was distilled off, the residue was crystallized by adding a small amount of ether to give colorless crystals of 2-methyl-7-[2-(1H-tetrazol-1-yl)acetamido]-3-cephem-4-carboxylic acid (0.97 g), mp 202° to 203° C. (dec.).

Workup

  1. temperaturecooling
  2. filtrationwas filtered off
  3. extractionthe filtrate was extracted
  4. additionby pouring into a matrix of ethyl acetate (50 ml), ice-water and 10% hydrochloric acid (5 ml)
  5. extractionThe aqueous layer was further extracted with ethyl acetate (10 ml)
  6. extractionthe ethyl acetate extract
  7. washwashed twice with water
  8. dry with materialdried over magnesium sulfate
  9. distillationAfter the solvent was distilled off
  10. customthe residue was crystallized
  11. additionby adding a small amount of ether

Sources & evidence

ORD record
ord-10e1044c04b14110a94b72eb53d7bb07
Source dataset
uspto-grants-1981_12
Patent number
US04308380

Reaction notes

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