Dimethylformamide → 7beta-(1H-tetrazol-1-yl)acetamido-3-[2-(N-carboethoxysulfamoyl)benzoyloxy]methyl-3-cephem-4-carboxylic acid

HRID 261718Notes

Reaction equation

HRID 261718 reaction equation
[NH2:1][C@@H:2]1[C:31](=[O:32])[N:4]2[C:5]([C:28]([OH:30])=[O:29])=[C:6]([CH2:9][O:10][C:11](=[O:27])[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[S:18](=[O:26])(=[O:25])[NH:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:7][S:8][C@H:3]12.ClCCl.CN(C)C=O.[N:41]1([CH2:46][C:47](Cl)=[O:48])[CH:45]=[N:44][N:43]=[N:42]1>O1CCCC1>[N:41]1([CH2:46][C:47]([NH:1][C@@H:2]2[C:31](=[O:32])[N:4]3[C:5]([C:28]([OH:30])=[O:29])=[C:6]([CH2:9][O:10][C:11](=[O:27])[C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=4[S:18](=[O:26])(=[O:25])[NH:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:7][S:8][C@H:3]23)=[O:48])[CH:45]=[N:44][N:43]=[N:42]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 13232854(1H-Tetrazol-1-yl)acetyl chlorideHCID 705835287beta-amino-3-[2-(N-carboethoxysulfamoyl)benzoyloxy]methyl-3-cephem-4-carboxylic acid

Product 1

HCID 705840957beta-(1H-tetrazol-1-yl)acetamido-3-[2-(N-carboethoxysulfamoyl)benzoyloxy]methyl-3-cephem-4-carboxylic acidYield 38.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

7β-Amino-3-[2-(N-carboethoxysulfamoyl)benzoyloxy]methyl-3-cephem-4-carboxylic acid (457 mg) is suspended in a mixed solution of dichloromethane (5 ml) and N,N-dimethylformamide (1.0 ml) and to the mixture, a solution of (1H-tetrazol-1-yl)acetyl chloride (161 mg) in tetrahydrofuran (2 ml) is added over a period of 20 minutes and stirred for 2 hours. The solvent is distilled off under reduced pressure and to the resultant viscous residue, ethyl acetate (50 ml) and water (20 ml) are added and stirred. After separation, the ethyl acetate layer is washed with water, dried over anhydrous sodium sulfate and concentrated. To the concentrate (5 ml), chloroform (50 ml) is added and the resultant precipitate is filtered off. The filtrate is concentrated and to the concentrate (5 ml), ether (50 ml) is added. The resultant precipitate is collected by filtration and dried over phosphorous pentoxide. The procedure provides 7β-(1H-tetrazol-1-yl)acetamido-3-[2-(N-carboethoxysulfamoyl)benzoyloxy]methyl-3-cephem-4-carboxylic acid (216 mg).

Workup

  1. distillationThe solvent is distilled off under reduced pressure
  2. additionto the resultant viscous residue, ethyl acetate (50 ml) and water (20 ml) are added
  3. stirringstirred
  4. customAfter separation
  5. washthe ethyl acetate layer is washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. concentrationTo the concentrate (5 ml), chloroform (50 ml)
  9. additionis added
  10. filtrationthe resultant precipitate is filtered off
  11. concentrationThe filtrate is concentrated
  12. concentrationto the concentrate (5 ml), ether (50 ml)
  13. additionis added
  14. filtrationThe resultant precipitate is collected by filtration
  15. dry with materialdried over phosphorous pentoxide

Sources & evidence

ORD record
ord-b1ff060d579d43b7a6f970e6e999d661
Source dataset
uspto-grants-1979_08
Patent number
US04166178

Reaction notes

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