Sulfuric Acid → HCID 14502320, compound

HRID 1248876Notes

Reaction equation

HRID 1248876 reaction equation
CC(O[CH2:5][C:6]1[CH2:15][S:14][C@@H:9]2[C@H:10]([NH2:13])[C:11](=[O:12])[N:8]2[C:7]=1[C:16]([OH:18])=[O:17])=O.B(F)(F)F.CC[O:25][CH2:26][CH3:27].[S:28]1[CH:32]=[CH:31][CH:30]=[C:29]1[CH2:33][C:34](Cl)=[O:35].S(=O)(=O)(O)O.C(#[N:44])C>CC(C)=O>[S:28]1[CH:32]=[CH:31][CH:30]=[C:29]1[CH2:33][C:34]([NH:13][CH:10]1[C:11](=[O:12])[N:8]2[C:7]([C:16]([OH:18])=[O:17])=[C:6]([CH2:5][NH:44][C:26](=[O:25])[CH3:27])[CH2:15][S:14][C@H:9]12)=[O:35]

Participants

7

Reactant 5

HCID 1118Sulfuric AcidHCID 6342AcetonitrileHCID 8000Boron trifluoride etherateHCID 1623622-Thiopheneacetyl chlorideHCID 4413287-Aminocephalosporanic acid

Product 1

HCID 14502320HCID 14502320, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
40 °C

Procedure

2.72 g. of 7-aminocephalosporanic acid (7-ACA) were suspended in 15 ml. of anhydrous acetonitrile and 5.68 g. of boron trifluoride etherate were added. The reaction mixture was stirred at 40° C. for 5 hours. The solvent was evaporated in vacuo and the residue as taken up with 30 ml. of water. The pH of the solution was adjusted to 3.5 by adding about 10 ml. of a 25% aqueous sodium hydroxide solution and the precipitate separated (the unreacted 7-ACA) was filtered off. The pH of the mixture was adjusted to 7 by adding potassium phosphate solution, thereafter the mixture was diluted with 10 ml. of acetone. 2.4 g. (0.015 moles) of 2-thienylacetyl chloride dissolved in 4 ml. of anhydrous acetone were added to the mixture dropwise at 0° to 5° C. and during the addition the pH of the mixture was maintained between 7 and 8. After the mixture had been stirred for a further hour at room temperature at a pH of 7 to 8 the reaction was accomplished. The pH of the reaction mixture was adjusted to 5 by adding some diluted sulphuric acid, and then the solution was extracted with 30 ml. of ethyl acetate. The pH of the aqueous phase was adjusted to 2 by adding some diluted sulphuric acid and the mixture was extracted with 60 ml. of ethyl acetate. The organic extract was dried over magnesium sulphate. The solvent was evaporated in vacuo, the residue was treated with ether, filtered and washed. 2.76 g. of 7-(2-thienyl)acetylamino-3-acetylaminomethylceph-3-em-4-carboxylic acid were obtained in powder form.

Workup

  1. customThe solvent was evaporated in vacuo
  2. additionby adding about 10 ml
  3. customof a 25% aqueous sodium hydroxide solution and the precipitate separated (the unreacted 7-ACA)
  4. filtrationwas filtered off
  5. additionby adding potassium phosphate solution
  6. additionthe mixture was diluted with 10 ml
  7. temperaturewas maintained between 7 and 8
  8. extractionthe solution was extracted with 30 ml
  9. additionby adding some diluted sulphuric acid
  10. extractionthe mixture was extracted with 60 ml
  11. extractionThe organic extract
  12. dry with materialwas dried over magnesium sulphate
  13. customThe solvent was evaporated in vacuo
  14. additionthe residue was treated with ether
  15. filtrationfiltered
  16. washwashed

Sources & evidence

ORD record
ord-45b15f41ded8436391b70e7e57a986a2
Source dataset
uspto-grants-1986_12
Patent number
US04626533

Reaction notes

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