Water → HCID 68132120, compound

HRID 1605404Notes

Reaction equation

HRID 1605404 reaction equation
[F:1][CH2:2][C:3]1[CH2:4][S:5](=O)[C@@H:6]2[CH:18]([NH:19][C:20](=[O:28])[CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:17](=[O:29])[N:7]2[C:8]=1[C:9]([O:11][CH2:12][C:13]([Cl:16])([Cl:15])[Cl:14])=[O:10].Cl[Sn]Cl.C(Cl)(=O)C.O>CC#N.CN(C=O)C>[F:1][CH2:2][C:3]1[CH2:4][S:5][C@@H:6]2[CH:18]([NH:19][C:20](=[O:28])[CH2:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:17](=[O:29])[N:7]2[C:8]=1[C:9]([O:11][CH2:12][C:13]([Cl:16])([Cl:15])[Cl:14])=[O:10]

Participants

7

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 24479Stannous ChlorideHCID 68131421HCID 68131421, compound

Product 1

HCID 68132120HCID 68132120, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 0.494 g (1.0 mmole) of 2,2,2-trichloroethyl 3-fluoromethyl-7-phenylacetamido-3-cephem-4-carboxylate-1-oxide in 5 ml CH3CN and 2 ml DMF at 0° is added 0.207 g (1.1 mmole) anhydrous SnCl2 and 0.40 g (5 mmole) acetyl chloride and the resulting mixture is stirred at 0° for 1.0 hrs, then at 25° for 1.0 hour, and then poured into water and extracted with ethyl acetate. The ethyl acetate layer is washed with 3% HCl solution, 5% NaHCO3 solution, and water, and then dried (MgSO4) and stripped in vacuo to give 2,2,2-trichloroethyl 3-fluoromethyl-7-phenylacetamido-3-cephem-4-carboxylate, which can be purified by chromatography on silica gel with chloroform.

Workup

  1. waitat 25° for 1.0 hour
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer is washed with 3% HCl solution, 5% NaHCO3 solution, and water
  4. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-b5e5275c135a415d8b15c9dd05559eab
Source dataset
uspto-grants-1976_04
Patent number
US03950329

Reaction notes

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