Iodine → HCID 13564037, compound

HRID 1248028Notes

Reaction equation

HRID 1248028 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][C@@H:10]1[C:35](=[O:36])[N:12]2[C:13]([C:22]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=3)=[O:23])=[C:14](OS(C)(=O)=O)[CH2:15][S:16][C@H:11]12)=[O:8].CN(C=O)C.[N-:42]=[N+:43]=[N-:44].[Na+].II>C1(C)C=CC=CC=1.C(OCC)(=O)C>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][C@@H:10]1[C:35](=[O:36])[N:12]2[C:13]([C:22]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=3)=[O:23])=[C:14]([N:42]=[N+:43]=[N-:44])[CH2:15][S:16][C@H:11]12)=[O:8]

Participants

7

Reactant 4

HCID 807IodineHCID 6228DimethylformamideHCID 33557Sodium AzideHCID 13564035HCID 13564035, compound

Product 1

HCID 13564037HCID 13564037, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of 0.554 g. of p-nitrobenzyl 7β-(2-thienylacetamido)-3-methylsulfonyloxy-3-cephem-4-carboxylate in 10 ml. of DMF was added one molar equivalent (0.065 g.) of sodium azide and the mixture stirred at room temperature for 30 minutes. The mixture was transferred to a separatory funnel with ethyl acetate and the solution was washed three times with water, once with brine, dried over sodium sulfate and evaporated to dryness. The product, 0.523 g, obtained as a yellow froth showed a single spot on silica gel thin layer chromatography using 1:1, ethyl acetate:toluene for development and iodine for visualization.

Workup

  1. washthe solution was washed three times with water
  2. dry with materialonce with brine, dried over sodium sulfate
  3. customevaporated to dryness
  4. customThe product, 0.523 g, obtained as a yellow froth

Sources & evidence

ORD record
ord-8099551cb6134e05963ede56fbb65c79
Source dataset
uspto-grants-1985_06
Patent number
US04521598

Reaction notes

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