Trifluoroacetic acid → HCID 131712706, compound

HRID 434873Notes

Reaction equation

HRID 434873 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:44]1[N:45]=[C:46]([NH:49][CH:50]=[O:51])[S:47][CH:48]=1)[C:5]([NH:7][CH:8]1[C:42](=[O:43])[N:10]2[C:11]([C:26]([O:28]C(C3C=CC=CC=3)C3C=CC=CC=3)=[O:27])=[C:12]([CH2:15][O:16][C:17]([N:19]3[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]3)=[O:18])[CH2:13][S:14][C@H:9]12)=[O:6].FC(F)(F)C([O-])=O.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:1][O:2][N:3]=[C:4]([C:44]1[N:45]=[C:46]([NH:49][CH:50]=[O:51])[S:47][CH:48]=1)[C:5]([NH:7][CH:8]1[C:42](=[O:43])[N:10]2[C:11]([C:26]([OH:28])=[O:27])=[C:12]([CH2:15][O:16][C:17]([N:19]3[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]3)=[O:18])[CH2:13][S:14][C@H:9]12)=[O:6]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 84468TrifluoroacetateHCID 131712707HCID 131712707, compound

Product 1

HCID 131712706HCID 131712706, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of benzhydryl 7-[2-methoxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-(4-methyl-1-piperazinyl)carbonyloxymethyl-3-cephem-4-carboxylate.trifluoroacetate (syn isomer) (1.4 g ) in methylene chloride (30 ml) were added anisole (1.4 ml) and trifluoroacetic acid (1.83 ml) with stirring under ice-cooling and the stirring was continued for 4 hours at 5° C. The reaction mixture was evaporated and the residual oil was pulverized in diethyl ether, collected by filtration and then dried to give 7-[2-methoxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-(4-methyl-1-piperazinyl)carbonyloxymethyl-3-cephem-4-carboxylic acid.trifluoroacetate (syn isomer) (1.1 g).

Workup

  1. temperaturecooling
  2. customThe reaction mixture was evaporated
  3. filtrationcollected by filtration
  4. customdried

Sources & evidence

ORD record
ord-99cfab19d69f4780bae731a769a0505f
Source dataset
uspto-grants-1983_08
Patent number
US04399278

Reaction notes

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