Dimethylformamide → HCID 131712319, compound

HRID 1758409Notes

Reaction equation

HRID 1758409 reaction equation
P(Cl)(Cl)(Cl)=O.CN(C)C=O.[CH:11]([NH:13][C:14]1[S:15][CH:16]=[C:17]([C:19](=[N:23][O:24][CH2:25][S:26][CH3:27])[C:20]([OH:22])=O)[N:18]=1)=[O:12].[NH2:28][CH:29]1[C:39](=[O:40])[N:31]2[C:32]([C:36]([OH:38])=[O:37])=[CH:33][CH2:34][S:35][C@H:30]12>C(OCC)(=O)C.O>[CH:11]([NH:13][C:14]1[S:15][CH:16]=[C:17]([C:19](=[N:23][O:24][CH2:25][S:26][CH3:27])[C:20]([NH:28][CH:29]2[C:39](=[O:40])[N:31]3[C:32]([C:36]([OH:38])=[O:37])=[CH:33][CH2:34][S:35][C@H:30]23)=[O:22])[N:18]=1)=[O:12]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 12941984(6R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidHCID 53744847HCID 53744847, compound

Product 1

HCID 131712319HCID 131712319, compoundYield 13.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent3×

Procedure

Phosphoryl chloride (0.754 g.) was added dropwise to a solution of N,N-dimethylformamide (0.36 g.) in ethyl acetate (2 ml.) at -10° to -5° C. and stirred at the same temperature for 30 minutes. Ethyl acetate (13 ml.) and 2-(2-formamidothiazol-4-yl)-2-methylthiomethoxyiminoacetic acid (syn isomer, 1.13 g.) were added to the mixture at -10° to -5° C. and stirred at the same temperature for 30 minutes to give an activated acid solution. The solution was added to a solution of 7-amino-3-cephem-4-carboxylic acid (0.82 g.) and bis(trimethylsilyl)acetamido (4.17 g.) in ethyl acetate (8.2 ml.) at -20° C. and the resulting reaction mixture was stirred at -10° to -5° C. for 30 minutes. After adding water to the resultant solution, the mixture was extracted twice with ethyl acetate. The extracts were washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and concentrated in vacuo. The residue was pulverized with diisopropyl ether, and the precipitates were collected by filtration and dried to give 7-[2-(2-formamidothiazol-4-yl)-2-methylthiomethoxyiminoacetamido]-3-cephem-4-carboxylic acid (syn isomer, 0.26 g.).

Workup

  1. stirringstirred at the same temperature for 30 minutes
  2. customto give an activated acid solution
  3. customthe resulting reaction mixture
  4. stirringwas stirred at -10° to -5° C. for 30 minutes
  5. extractionthe mixture was extracted twice with ethyl acetate
  6. washThe extracts were washed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. filtrationthe precipitates were collected by filtration
  10. customdried

Sources & evidence

ORD record
ord-417e65eed5c04beca0de78e2d78fdad7
Source dataset
uspto-grants-1983_02
Patent number
US04372952

Reaction notes

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