Acetyl chloride → HCID 131710495, compound

HRID 972491Notes

Reaction equation

HRID 972491 reaction equation
[CH2:1]([O:3][N:4]=[CH:5][C:6]1[CH2:7][S:8](=O)[C@@H:9]2[CH:16]([NH:17][C:18](=[O:25])[CH2:19][C:20]3[S:21][CH:22]=[CH:23][CH:24]=3)[C:15](=[O:26])[N:10]2[C:11]=1[C:12]([OH:14])=[O:13])[CH3:2].C(Cl)(=O)C>CN(C)C=O>[CH2:1]([O:3][N:4]=[CH:5][C:6]1[CH2:7][S:8][C@@H:9]2[CH:16]([NH:17][C:18](=[O:25])[CH2:19][C:20]3[S:21][CH:22]=[CH:23][CH:24]=3)[C:15](=[O:26])[N:10]2[C:11]=1[C:12]([OH:14])=[O:13])[CH3:2]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 131710496HCID 131710496, compound

Product 1

HCID 131710495HCID 131710495, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-ethoxyiminomethyl-7-(2-thienylacetamido)-3-cephem-4-carboxylic acid-1-oxide (100 mg) in N,N-dimethylformamide (5 ml) is added stannous chloride (100 mg) at 0° C. under nitrogen atmosphere, and acetyl chloride (0.8 ml) is added dropwise to the stirred mixture. After 90 minutes, the reaction mixture is added a few piece of ice, and stirred for 10 minutes, and then extracted with ethyl acetate. The extract solution is washed with saturated saline solution and saturated aqueous sodium hydrogen carbonate, dried and evaporated to give residue which on recrystallization from a mixture of methylene chloride and ether gives 3-ethoxyiminomethyl-7-(2-thienylacetamido)-3-cephem-4-carboxylic acid. m.p. 177°-183° C. (decomp.).

Workup

  1. additionthe reaction mixture is added a few piece of ice
  2. extractionextracted with ethyl acetate
  3. washThe extract solution is washed with saturated saline solution and saturated aqueous sodium hydrogen carbonate
  4. customdried
  5. customevaporated
  6. customto give residue which
  7. customon recrystallization
  8. additionfrom a mixture of methylene chloride and ether

Sources & evidence

ORD record
ord-3096a67345c945f9964ab752c783cdca
Source dataset
uspto-grants-1977_10
Patent number
US04053469

Reaction notes

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