Triethylamine → HCID 131714984, compound

HRID 1248879Notes

Reaction equation

HRID 1248879 reaction equation
BrCC(N[CH:6]1[C:21](=[O:22])[N:8]2[C:9]([C:18]([OH:20])=[O:19])=[C:10]([CH2:13][NH:14][C:15](=[O:17])[CH3:16])[CH2:11][S:12][C@H:7]12)=O.[CH3:23][N:24]1[C:28]([SH:29])=[N:27][N:26]=[N:25]1.[CH2:30]([N:32](CC)CC)[CH3:31].C(=O)([O-])[O-:38].[K+].[K+]>CCOCC.CN(C)C=O>[CH3:23][N:24]1[C:28]([S:29][CH:6]2[C:21](=[O:22])[N:8]3[C:9]([C:18]([OH:20])=[O:19])=[C:10]([CH2:13][NH:14][C:15](=[O:17])[CH3:16])[CH:11]([NH:32][C:30](=[O:38])[CH3:31])[S:12][C@H:7]23)=[N:27][N:26]=[N:25]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 70468832HCID 70468832, compoundHCID 178482017HCID 178482017, compound

Product 1

HCID 131714984HCID 131714984, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

1.0 g. of 7-bromoacetamido-3-acetylaminomethylceph-3-em-4-carboxylic acid, 0.3 g. of 1-methyl-5-mercapto-1H-tetrazole and 9.1 g. of triethyl amine were dissolved in 20 ml. of anhydrous dimethyl formamide. The reaction mixture was stirred at room temperature for 12 hours. First 0.7 g. of calcinated potassium carbonate, then 30 ml. of ether were added to the reaction mixture. The precipitate separated was filtered off, dissolved in water, the pH of the solution was adjusted to 2 by adding diluted sulphuric acid and the mixture was extracted with ethyl acetate. The organic extract was dried over anhydrous magnesium sulphate. The solvent was evaporated in vacuo and the residue was treated with diethyl ether. Thus 0.76 g. of 7-(1-methyl-1H-tetrazole-5-ylthio)-acetamido-3-acetylaminomethylceph-3-em-4-carboxylic acid were obtained.

Workup

  1. customThe precipitate separated
  2. filtrationwas filtered off
  3. dissolutiondissolved in water
  4. additionby adding diluted sulphuric acid
  5. extractionthe mixture was extracted with ethyl acetate
  6. extractionThe organic extract
  7. dry with materialwas dried over anhydrous magnesium sulphate
  8. customThe solvent was evaporated in vacuo
  9. additionthe residue was treated with diethyl ether

Sources & evidence

ORD record
ord-5b988c5bee5542cbb9527c5a6698e2e9
Source dataset
uspto-grants-1986_12
Patent number
US04626533

Reaction notes

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