Pyridine → HCID 131712938, compound

HRID 1164422Notes

Reaction equation

HRID 1164422 reaction equation
[CH3:1][C:2]1[CH2:3][S:4][C@@H:5]2[C:17](=O)[C:16](=[O:19])[N:6]2[C:7]=1[C:8]([O:10][CH2:11][C:12]([Cl:15])([Cl:14])[Cl:13])=[O:9].Cl.[CH3:21][O:22][NH2:23].N1C=CC=CC=1.C(Cl)Cl>CN(C)C=O>[CH3:21][O:22][N:23]=[C:17]1[C:16](=[O:19])[N:6]2[C:7]([C:8]([O:10][CH2:11][C:12]([Cl:15])([Cl:14])[Cl:13])=[O:9])=[C:2]([CH3:1])[CH2:3][S:4][C@H:5]12

Participants

6

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 521874O-Methylhydroxylamine hydrochlorideHCID 70464109HCID 70464109, compound

Product 1

HCID 131712938HCID 131712938, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In dimethylformamide (20 ml) are dissolved 2,2,2-trichloroethyl 3-methyl-7-oxo-3-cephem-4-carboxylate (3.63 g) and methoxyamine hydrochloride (2.63 g), followed by addition of pyridine (0.83 g) and methylene chloride (70 ml). The mixture is refluxed in a Dean-Stark trap packed with Molecular Sieve 3A for 2 hours. The reaction mixture is concentrated under reduced pressure and the residue is dissolved in ethyl acetate. This solution is washed with water, 1 N-HCl and aqueous sodium chloride in the order mentioned, dried over magnesium sulfate and concentrated under reduced pressure. The residual oil is subjected to silica gel (35 g) column chromatography and elution is carried out with methylene chloride. By the above procedure is obtained 2,2,2-trichloroethyl 7-methoxyimino-3-methyl-3-cephem-4-carboxylate as as oil (3.66 g).

Workup

  1. temperatureThe mixture is refluxed in a Dean-Stark trap
  2. concentrationThe reaction mixture is concentrated under reduced pressure
  3. dissolutionthe residue is dissolved in ethyl acetate
  4. washThis solution is washed with water, 1 N-HCl and aqueous sodium chloride in the order
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. washThe residual oil is subjected to silica gel (35 g) column chromatography and elution

Sources & evidence

ORD record
ord-ae2b11e616954e8389fb1d8526d58017
Source dataset
uspto-grants-1983_01
Patent number
US04369312

Reaction notes

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