Acetyl chloride → HCID 131710495, compound

HRID 1287991Notes

Reaction equation

HRID 1287991 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-4carboxylic 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-6f94b5032af64c718c3e642091a45142
Source dataset
uspto-grants-1976_10
Patent number
US03987039

Reaction notes

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