Trifluoroacetic acid → HCID 131714842, compound

HRID 64749Notes

Reaction equation

HRID 64749 reaction equation
FC(F)(F)C(O)=O.C([O:21][C:22]([CH2:24][O:25][N:26]=[C:27]([C:61]1[N:62]=[C:63]([NH2:66])[S:64][CH:65]=1)[C:28]([NH:30][CH:31]1[C:59](=[O:60])[N:33]2[C:34]([C:43]([O:45]C(C3C=CC=CC=3)C3C=CC=CC=3)=[O:44])=[C:35]([CH:39]=[C:40]([F:42])[F:41])[CH2:36][S:37](=[O:38])[C@H:32]12)=[O:29])=[O:23])(C1C=CC=CC=1)C1C=CC=CC=1.C1(OC)C=CC=CC=1.C(OC(C)C)(C)C>C(Cl)Cl>[C:22]([CH2:24][O:25][N:26]=[C:27]([C:61]1[N:62]=[C:63]([NH2:66])[S:64][CH:65]=1)[C:28]([NH:30][CH:31]1[C:59](=[O:60])[N:33]2[C:34]([C:43]([OH:45])=[O:44])=[C:35]([CH:39]=[C:40]([F:41])[F:42])[CH2:36][S:37](=[O:38])[C@H:32]12)=[O:29])([OH:23])=[O:21]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 7914Diisopropyl EtherHCID 131714843HCID 131714843, compound

Product 1

HCID 131714842HCID 131714842, compoundYield 27.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (0.805 g) was added to a suspension of benzhydryl 7-[2-benzhydryloxycarbonylmethoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-(2,2-difluorovinyl)-3-cephem-4-carboxylate-1-oxide (syn isomer) (0.3 g) in methylene chloride (0.6 ml) and anisole (0.382 g) under ice-cooling and the mixture was stirred at the same temperature for 30 minutes. The reaction mixture was dropwise added to diisopropylether (10 ml) and the precipitates were collected by filtration. The precipitates were added to a mixture of ethyl acetate and water and the mixture was adjusted to pH 7.0 with saturated aqueous sodium bicarbonate. The separated aqueous layer was acidified to pH 3.0 with 10% hydrochloric acid and the precipitates were collected by filtration to give 7-[2-carboxymethoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-(2,2-difluorovinyl)-3-cephem-4-carboxylic acid-1-oxide (syn isomer) (0.05 g).

Workup

  1. temperaturecooling
  2. filtrationthe precipitates were collected by filtration
  3. additionThe precipitates were added to a mixture of ethyl acetate and water
  4. filtrationthe precipitates were collected by filtration

Sources & evidence

ORD record
ord-fa109d861a4345abb1bd3a51a94e2dca
Source dataset
uspto-grants-1986_09
Patent number
US04609730

Reaction notes

Loading…