Trifluoroacetic acid → HCID 131718065, compound

HRID 2253998Notes

Reaction equation

HRID 2253998 reaction equation
C(NC1SC=C(/C(=N/OC(C(OC(C2C=CC=CC=2)C2C=CC=CC=2)=O)C2C=CC(OC(=O)C)=C(OC(=O)C)C=2)/C(N[C@@H:30]2[C:57](=[O:58])[N:32]3[C:33]([C:45]([O:47]CC4C=CC(OC)=CC=4)=[O:46])=[C:34]([CH:37]=[CH:38][C:39]4[S:43][CH:42]=[N:41][C:40]=4[CH3:44])[CH2:35][S:36][C@H:31]23)=O)N=1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1(OC)C=CC=CC=1.[F:100][C:101]([F:106])([F:105])[C:102]([OH:104])=[O:103]>C(Cl)Cl>[F:100][C:101]([F:106])([F:105])[C:102]([OH:104])=[O:103].[CH3:44][C:40]1[N:41]=[CH:42][S:43][C:39]=1[CH:38]=[CH:37][C:34]1[CH2:35][S:36][C@@H:31]2[CH2:30][C:57](=[O:58])[N:32]2[C:33]=1[C:45]([OH:47])=[O:46]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acid2×HCID 7519AnisoleHCID 178491511HCID 178491511, compound

Product 1

HCID 131718065HCID 131718065, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

709 mg (0.558 mmol) of 4-methoxybenzyl 7β-[(Z)-2-(2-tritylamino-4-thiazolyl)-2-[[(R S)-(diphenylmethoxy carbonyl)(3,4-diacetoxyphenyl)methoxyl]imino]acetamido]-3-[2-(4-methyl-5-thiazolyl)vinyl]-3-cephem-4-carboylate was dissolved in 7 ml of methylene chloride and 2.8 ml of anisole and then 11.2 ml of trifluoroacetic acid was added under and then 11.2 ml of trifluoroacetic acid was added under ice-cooling and the reaction was performed for 90 min. Methylene chloride and trifluoroacetic acid were evaporated under the reduced pressure and the resultant residue was powdered with ethyl ether-hexane(1:1). The powder collected by filtration was further dissolved in 40 ml of trifluoroacetic acid under ice-cooling and then 10 ml of water was added and the reaction was performed for 2.5 hrs. at the room temperature. Trifluoroacetic acid and water were evaporated under the reduced pressure and to the resultant residue was added ethyl ether to powder and collected by filtration to give 298 mg of 7β -[(Z)-2-(2-amino-4-thiazolyl)-2[[(R S)-carboxy)(3,4-diacetoxyphenyl)methoxy]imino]acetamido]-3-[2-(4-methyl-5-thiazolyl)vinyl]-3-cephem-4-carboxylic acid trifluoroacetate.

Workup

  1. additionwas added under ice-
  2. temperaturecooling
  3. customMethylene chloride and trifluoroacetic acid were evaporated under the reduced pressure
  4. filtrationThe powder collected by filtration
  5. dissolutionwas further dissolved in 40 ml of trifluoroacetic acid under ice-
  6. temperaturecooling
  7. addition10 ml of water was added
  8. waitthe reaction was performed for 2.5 hrs
  9. customat the room temperature
  10. customTrifluoroacetic acid and water were evaporated under the reduced pressure and to the resultant residue
  11. additionwas added ethyl ether to powder
  12. filtrationcollected by filtration

Sources & evidence

ORD record
ord-5780741c7792449d9eed877ddafff639
Source dataset
uspto-grants-1993_08
Patent number
US05233035

Reaction notes

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