Dimethylformamide → 4-Nitrobenzyl 7-[2-(2-formamido-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate

HRID 621348Notes

Reaction equation

HRID 621348 reaction equation
S(Cl)(C)(=O)=O.[CH:6]([NH:8][C:9]1[S:10][CH:11]=[C:12]([C:14](=[N:41][O:42][CH3:43])[C:15]([NH:17][CH:18]2[C:39](=[O:40])[N:20]3[CH:21]([C:26]([O:28][CH2:29][C:30]4[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[CH:32][CH:31]=4)=[O:27])[CH:22](O)[CH2:23][S:24][C@H:19]23)=[O:16])[N:13]=1)=[O:7].CN(C)C=O.C(=O)([O-])[O-].[K+].[K+]>O.C(OCC)(=O)C>[CH:6]([NH:8][C:9]1[S:10][CH:11]=[C:12]([C:14](=[N:41][O:42][CH3:43])[C:15]([NH:17][CH:18]2[C:39](=[O:40])[N:20]3[C:21]([C:26]([O:28][CH2:29][C:30]4[CH:31]=[CH:32][C:33]([N+:36]([O-:38])=[O:37])=[CH:34][CH:35]=4)=[O:27])=[CH:22][CH2:23][S:24][C@H:19]23)=[O:16])[N:13]=1)=[O:7]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 1317124974-Nitrobenzyl 7-[2-(2-formamido-4-thiazolyl)-2-methoxyiminoacetamido]-3-hydroxycepham-4-carboxylate

Product 1

HCID 1317124414-Nitrobenzyl 7-[2-(2-formamido-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylateYield 12.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Mesyl chloride (0.406 g.) was dropwise added to a stirred mixture of 4-nitrobenzyl 7-[2-(2-formamido-4-thiazolyl)-2-methoxyiminoacetamido]-3-hydroxycepham-4-carboxylate (syn isomer, 1 g.), N,N-dimethylformamide (10 ml.) and potassium carbonate (0.732 g.) at 0° to 5° C. over 2 minutes, and the solution was stirred at room temperature for 2.5 hours. After ethyl acetate and water were added to the resultant solution, the soluttion was extracted with ethyl acetate. The remaining aqueous layer was extracted again with ethyl acetate. The ethyl acetate extract solution was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel (30 g.) and eluted with a mixture of chloroform and ethyl acetate. The eluate was concentrated under reduced pressure to give 4-nitrobenzyl 7-[2-(2-formamido-4-thiazolyl)-2 -methoxyiminoacetamido]-3-cephem-4-carboxylate (syn isomer, 0.12 g.), mp 224° C. (dec.).

Workup

  1. extractionthe soluttion was extracted with ethyl acetate
  2. extractionThe remaining aqueous layer was extracted again with ethyl acetate
  3. extractionThe ethyl acetate extract solution
  4. washwas washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. washeluted with a mixture of chloroform and ethyl acetate
  8. concentrationThe eluate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8393b9951db140118f6b11faa132397d
Source dataset
uspto-grants-1989_04
Patent number
US04822888

Reaction notes

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