Trifluoroacetic acid → 7-(2-Thienylacetamido)-3-(1-acetoxyethyl)-3-cephem-4-carboxylic acid

HRID 596837Notes

Reaction equation

HRID 596837 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:39](=[O:40])[N:12]2[C:13]([C:23]([O:25]C(C3C=CC=CC=3)C3C=CC=CC=3)=[O:24])=[C:14]([CH:17]([O:19][C:20](=[O:22])[CH3:21])[CH3:18])[CH2:15][S:16][C@H:11]12)=[O:8].C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O.CCCCCCC>CC(C)=O>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:39](=[O:40])[N:12]2[C:13]([C:23]([OH:25])=[O:24])=[C:14]([CH:17]([O:19][C:20](=[O:22])[CH3:21])[CH3:18])[CH2:15][S:16][C@H:11]12)=[O:8]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 8900HeptaneHCID 70617769Diphenylmethyl 7-(2-thienylacetamido)-3-(1-acetoxyethyl)-3-cephem-4-carboxylate

Product 1

HCID 706176497-(2-Thienylacetamido)-3-(1-acetoxyethyl)-3-cephem-4-carboxylic acidYield 40.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
5 °C

Procedure

To a cooled (5° C.), stirred solution of 0.328 g. of benzhydryl 7-(2-thienylacetamido)-3-(1-acetoxyethyl)-3-cephem-4-carboxylate in 1 ml. of anisole was added 1 ml. of cold trifluoroacetic acid. The reaction mixture was allowed to stir with cooling for 20 minutes after which time was added 30 ml. of n-heptane. The reaction mixture was evaporated in vacuo to a low volume, 20 ml. of n-heptane was added, and the resulting mixture was stirred with cooling for five minutes. The solid obtained by filtration of the resulting solution was dissolved in acetone, and the acetone solution was then filtered and evaporated to near dryness. The residue was dissolved in ethyl acetate, and the resulting solution was extracted three times with cold aqueous sodium bicarbonate solution. The aqueous extracts were combined, layered with ethyl acetate, and acidified with 1N.HCl. The organic layer was separated, washed with brine, and dried over anhydrous sodium sulfate. Evaporation in vacuo to dryness gave 94 mg. (40.5 percent) of the title product:

Workup

  1. stirringto stir
  2. temperaturewith cooling for 20 minutes after which time
  3. additionwas added 30 ml
  4. customThe reaction mixture was evaporated in vacuo to a low volume, 20 ml
  5. additionof n-heptane was added
  6. stirringthe resulting mixture was stirred
  7. temperaturewith cooling for five minutes
  8. customThe solid obtained by filtration of the resulting solution
  9. filtrationthe acetone solution was then filtered
  10. customevaporated
  11. dissolutionThe residue was dissolved in ethyl acetate
  12. extractionthe resulting solution was extracted three times with cold aqueous sodium bicarbonate solution
  13. customThe organic layer was separated
  14. washwashed with brine
  15. dry with materialdried over anhydrous sodium sulfate
  16. customEvaporation in vacuo to dryness
  17. customgave 94 mg

Sources & evidence

ORD record
ord-0a26186a70b3485a9d971caa6bd878d0
Source dataset
uspto-grants-1977_03
Patent number
US04012380

Reaction notes

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