Trifluoroacetic acid → HCID 131712599, compound

HRID 1659773Notes

Reaction equation

HRID 1659773 reaction equation
FC(F)(F)C(O)=O.C([O:12][C:13]([CH2:15][O:16][N:17]=[C:18]([C:41]1[N:42]=[C:43]([NH2:46])[S:44][CH:45]=1)[C:19]([NH:21][CH:22]1[C:39](=[O:40])[N:24]2[C:25]([C:36]([OH:38])=[O:37])=[C:26]([CH2:29][S:30][C:31]3[S:32][CH:33]=[N:34][N:35]=3)[CH2:27][S:28][C@H:23]12)=[O:20])=[O:14])(C)(C)C>C1(OC)C=CC=CC=1>[C:13]([CH2:15][O:16][N:17]=[C:18]([C:41]1[N:42]=[C:43]([NH2:46])[S:44][CH:45]=1)[C:19]([NH:21][CH:22]1[C:39](=[O:40])[N:24]2[C:25]([C:36]([OH:38])=[O:37])=[C:26]([CH2:29][S:30][C:31]3[S:32][CH:33]=[N:34][N:35]=3)[CH2:27][S:28][C@H:23]12)=[O:20])([OH:14])=[O:12]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131712598HCID 131712598, compound

Product 1

HCID 131712599HCID 131712599, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

Trifluoroacetic acid (4 ml.) was added under ice-cooling to a stirred suspension of 7-[2-t-butoxycarbonylmethoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer) (1.0 g.) in anisole (1 ml.), and the resultant mixture was stirred for 70 minutes at ambient temperature. The reaction mixture was concentrated under reduced pressure and diethyl ether was added thereto. Precipitates were collected by filtration, washed with diethyl ether, dried, suspended in water (10 ml.) and then dissolved in a 10% aqueous solution of sodium hydroxide (pH 7-7.5). The solution was adjusted to pH 3.0 with 10% hydrochloric acid under ice-cooling and stirring and stirred for 30 minutes under ice-cooling. Precipitates were collected by filtration, washed with water and dried to give 7-[2-carboxymethoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer) (0.75 g.).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure and diethyl ether
  2. additionwas added
  3. customPrecipitates
  4. filtrationwere collected by filtration
  5. washwashed with diethyl ether
  6. customdried
  7. dissolutiondissolved in a 10% aqueous solution of sodium hydroxide (pH 7-7.5)
  8. temperaturecooling
  9. stirringstirred for 30 minutes under ice-
  10. temperaturecooling
  11. customPrecipitates
  12. filtrationwere collected by filtration
  13. washwashed with water
  14. customdried

Sources & evidence

ORD record
ord-290c25bb4a04492da96dae51fdc877d1
Source dataset
uspto-grants-1981_12
Patent number
US04304770

Reaction notes

Loading…