Trifluoroacetic acid → HCID 131711752, compound

HRID 1089925Notes

Reaction equation

HRID 1089925 reaction equation
FC(F)(F)C(O)=O.[CH3:8][O:9][N:10]=[C:11]([C:35]1[N:36]=[C:37]([NH:40]C(OC(CC)(C)C)=O)[S:38][CH:39]=1)[C:12]([NH:14][CH:15]1[C:33](=[O:34])[N:17]2[C:18]([C:30]([OH:32])=[O:31])=[C:19]([CH2:22][S:23][C:24]3[S:25][C:26]([CH3:29])=[N:27][N:28]=3)[CH2:20][S:21][C@H:16]12)=[O:13]>>[CH3:8][O:9][N:10]=[C:11]([C:35]1[N:36]=[C:37]([NH2:40])[S:38][CH:39]=1)[C:12]([NH:14][CH:15]1[C:33](=[O:34])[N:17]2[C:18]([C:30]([OH:32])=[O:31])=[C:19]([CH2:22][S:23][C:24]3[S:25][C:26]([CH3:29])=[N:27][N:28]=3)[CH2:20][S:21][C@H:16]12)=[O:13]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131712300HCID 131712300, compound

Product 1

HCID 131711752HCID 131711752, compoundYield 31.1%

Procedure

Trifluoroacetic acid (3 ml) was added under ice-cooling to 7-[2-methoxyimino-2-(2-t-pentyloxycarbonylamino-1,3-thiazol-4-yl)acetamido]-3-(5-methyl-1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer) (0.5 g) and the mixture was stirred for 30 minutes at ambient temperature. To the mixture was added either and precipitating powder was collected by filtration and dissolved in a mixture of water (20 ml) and an 1N aqueous solution of sodium hydroxide to adjust to pH 12 to 13. The solution was adjusted to pH 4.6 with 10% hydrochloric acid, washed with ethyl acetate and methylene chloride. Excess methylene chloride in the aqueous layer was thoroughly removed by bubbling of nitrogen gas. The aqueous layer was adjusted to pH 2 with stirring and ice-cooling to precipitate powder. The powder was collected by filtration and dried to give 7-[2-methoxyimino-2-(2-amino-1,3-thiazol-4-yl)acetamido]-3-(5-methyl-1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer) (0.128 g).

Workup

  1. additionTo the mixture was added either
  2. customprecipitating powder
  3. filtrationwas collected by filtration
  4. dissolutiondissolved in a mixture of water (20 ml)
  5. washwashed with ethyl acetate and methylene chloride
  6. customExcess methylene chloride in the aqueous layer was thoroughly removed
  7. customby bubbling of nitrogen gas
  8. stirringwith stirring
  9. temperatureice-cooling
  10. customto precipitate powder
  11. filtrationThe powder was collected by filtration
  12. customdried

Sources & evidence

ORD record
ord-e79617a6748a4bc1884a4c6367d7c43c
Source dataset
uspto-grants-1992_01
Patent number
US05079369

Reaction notes

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