Dimethylformamide → HCID 131714473, compound

HRID 1285099Notes

Reaction equation

HRID 1285099 reaction equation
[C:1]([NH:4][C@@H:5]1[C:17](=[O:18])[N:7]2[C:8]([C:13]([O:15][CH3:16])=[O:14])=[C:9](Cl)[CH2:10][S:11][C@H:6]12)(=[O:3])[CH3:2].CN(C=O)C.[N-:24]=[N+:25]=[N-:26].[Na+]>C(OCC)(=O)C>[C:1]([NH:4][C@@H:5]1[C:17](=[O:18])[N:7]2[C:8]([C:13]([O:15][CH3:16])=[O:14])=[C:9]([N:24]=[N+:25]=[N-:26])[CH2:10][S:11][C@H:6]12)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 33557Sodium AzideHCID 70467723HCID 70467723, compound

Product 1

HCID 131714473HCID 131714473, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 0.784 g. of methyl 7β-acetamido-3-chloro-3-cephem-4-carboxylate in 40 ml. of DMF was cooled to 5° C. in an ice bath and 0.193 g. of sodium azide were added. The reaction mixture was stirred in the cold for 45 minutes and then transferred to a separatory funnel with ethyl acetate. The mixture was washed with cold water, with brine, and was dried and evaporated to dryness. There were obtained 0.581 g. of the 3-azido ester product as a yellow solid.

Workup

  1. washThe mixture was washed with cold water, with brine
  2. customwas dried
  3. customevaporated to dryness
  4. customThere were obtained 0.581 g

Sources & evidence

ORD record
ord-e357b44b3e844707985315da187e9d17
Source dataset
uspto-grants-1986_01
Patent number
US04565655

Reaction notes

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