Trifluoroacetate → HCID 178475421, compound

HRID 2253996Notes

Reaction equation

HRID 2253996 reaction equation
C([NH:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:58]/[O:59][CH:60]([C:75]([O:77]C(C2C=CC=CC=2)C2C=CC=CC=2)=[O:76])[C:61]2[CH:66]=[CH:65][C:64]([O:67][C:68](=[O:70])[CH3:69])=[C:63]([O:71][C:72](=[O:74])[CH3:73])[CH:62]=2)/[C:27]([NH:29][C@@H:30]2[C:56](=[O:57])[N:32]3[C:33]([C:44]([O:46]CC4C=CC(OC)=CC=4)=[O:45])=[C:34]([CH:37]=[CH:38][C:39]4[CH:43]=[CH:42][S:41][N:40]=4)[CH2:35][S:36][C@H:31]23)=[O:28])[N:25]=1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.FC(F)(F)C([O-])=O>C(Cl)Cl.C1(OC)C=CC=CC=1>[NH2:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:58]/[O:59][CH:60]([C:75]([OH:77])=[O:76])[C:61]2[CH:66]=[CH:65][C:64]([O:67][C:68](=[O:70])[CH3:69])=[C:63]([O:71][C:72](=[O:74])[CH3:73])[CH:62]=2)/[C:27]([NH:29][C@@H:30]2[C:56](=[O:57])[N:32]3[C:33]([C:44]([OH:46])=[O:45])=[C:34]([CH:37]=[CH:38][C:39]4[CH:43]=[CH:42][S:41][N:40]=4)[CH2:35][S:36][C@H:31]23)=[O:28])[N:25]=1

Participants

5

Reactant 2

HCID 84468TrifluoroacetateHCID 178491508HCID 178491508, compound

Product 1

HCID 178475421HCID 178475421, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7519AnisoleSolvent

Procedure

After 400 mg of p-methoxybenzyl 7β-[(Z)-2-(2-tritylamino-4-thiazolyl)-2-[[(R S)-(diphenylmethoxycarbonyl)(3,4-diacetoxyphenyl)methoxy]imino]acetamido]-3-[2-(isothiazol-3-yl)vinyl]-3-cephem-4-carboxylate were dissolved in 4 ml of methylene chloride and 2 ml of anisole, 8 ml of trifluoroacetate was added therein under ice-cooling, and the reaction solution was reacted for 90 min. as it was. The residue obtained by evaporating off methylene chloride and trifluoroacetate was powdered by using ethyl ether. The powder obtained by filtering off was further added to 24 ml of trifluoroacetate under ice-cooling, and then 6 ml of water was added therein, and the reactants were reacted for 30 min. as they were, and further reacted for 2 hrs. at the room temperature. The residue obtained by evaporating off trifluoroacetate and water under the reduced pressure was powdered by adding ethyl ether and filtered off to give 190 mg of 7β-[(Z)-2-(2-amino-4-thiazolyl)-2-[ [(R S)-(carboxy)(3,4-diacetoxyphenyl)methoxy]imino]acetamido]-3-[2-(isothiazol-3-yl)vinyl]-3-cephem-4-carboxylic acid.trifluoroacetate.

Workup

  1. temperatureunder ice-cooling
  2. customthe reaction solution was reacted for 90 min. as it
  3. customThe residue obtained
  4. customby evaporating off methylene chloride and trifluoroacetate
  5. customThe powder obtained
  6. filtrationby filtering off
  7. additionwas further added to 24 ml of trifluoroacetate under ice-
  8. temperaturecooling
  9. addition6 ml of water was added
  10. customthe reactants were reacted for 30 min. as they
  11. customfurther reacted for 2 hrs
  12. customat the room temperature
  13. customThe residue obtained
  14. customby evaporating off trifluoroacetate and water under the reduced pressure
  15. additionby adding ethyl ether
  16. filtrationfiltered off

Sources & evidence

ORD record
ord-9a79a0fc3bd64fd88029044e7af1b5e4
Source dataset
uspto-grants-1993_08
Patent number
US05233035

Reaction notes

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