Trifluoroacetic acid → HCID 178475422, compound

HRID 2253993Notes

Reaction equation

HRID 2253993 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[S:43][CH:42]=[N:41][CH: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[S:43][CH:42]=[N:41][CH:40]=4)[CH2:35][S:36][C@H:31]23)=[O:28])[N:25]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178491509HCID 178491509, compound

Product 1

HCID 178475422HCID 178475422, compoundYield 80.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7519AnisoleSolvent

Procedure

After 870 mg (0.69 mmol) of p-methoxybenzyl 7β-[(Z)-2-(2-tritylamino-4-thiazolyl)-2-[[(R S)-(diphenylmethoxycarbonyl)(3,4-diacetoxyphenyl)methoxy]imino]acetamido]-3-[-2-(5-thiazolyl)vinyl]-3-cephem-4-carboxylate was dissolved in 9 ml of methylene chloride and 4 ml of anisole, 16 ml of trifluoroacetic acid was added therein under ice-cooling and the reaction solution was reacted for 90 min. as it was. The residue obtained by evaporating off trifluoroacetate under the reduced pressure was powdered with ethyl ether-hexane (1:1). The powder obtained by filtering off was further dissolved in 45 ml of trifluoroacetic acid under ice-cooling, and then, 11 ml of water was added therein, and the reaction was effected for 3 hrs. at the room temperature. The residue obtained by evaporating off trifluoroacetic acid and water under the reduced pressure was powdered by adding ethyl ether, and filtered off to give 404 mg of 7β-[(Z)-2-(2-amino-4-thiazolyl)-2-[[(R S)-(carboxy) (3,4 -diacetoxyphenyl)methoxy]imino]acetamido]-3-[-2-(5-thiazolyl)vinyl]-3-cephem-4-carboxylic acid.trifluoroacetate, a crude product.

Workup

  1. temperatureunder ice-cooling
  2. customthe reaction solution was reacted for 90 min. as it
  3. customThe residue obtained
  4. customby evaporating off trifluoroacetate under the reduced pressure
  5. customThe powder obtained
  6. filtrationby filtering off
  7. dissolutionwas further dissolved in 45 ml of trifluoroacetic acid under ice-
  8. temperaturecooling
  9. addition11 ml of water was added
  10. customat the room temperature
  11. customThe residue obtained
  12. customby evaporating off trifluoroacetic acid and water under the reduced pressure
  13. additionby adding ethyl ether
  14. filtrationfiltered off

Sources & evidence

ORD record
ord-3baaf976b0bc4827b9af33838348daf5
Source dataset
uspto-grants-1993_08
Patent number
US05233035

Reaction notes

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