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Trifluoroacetic acid → 7-Amino-3-cephem-4-carboxylic acid

HRID 1903575
Notes
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Reaction equation

HRID 1903575 reaction equation
C([O:14][C:15]([C:17]1[N:22]2[C:23](=[O:26])[C@@H:24]([NH2:25])[C@H:21]2[S:20][CH2:19][CH:18]=1)=[O:16])(C1C=CC=CC=1)C1C=CC=CC=1.FC(F)(F)C(O)=O>C1(OC)C=CC=CC=1.C1(C)C=CC=CC=1>[NH2:25][C@@H:24]1[C:23](=[O:26])[N:22]2[C:17]([C:15]([OH:16])=[O:14])=[CH:18][CH2:19][S:20][C@H:21]12
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 9842110diphenylmethyl (6R,7R)-7-Amino-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate

Product 1

HCID 117357907-Amino-3-cephem-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 7519AnisoleSolvent

Procedure

36.6 g of 7β-amino-3-cephem-4-carboxylic acid benzhydryl ester in 60 ml of anisole are reacted for 10 minutes at room temperature with 240 ml of trifluoroacetic acid. The reaction mixture is diluted with toluene and evaporated to dryness in vacuo. The residue is dissolved in a mixture of 150 ml of methanol, 250 ml of ether and 10 ml of water and the pH is adjusted to 3.5 with triethylamine. The suspension is cooled for 1 hour to 0° C. and the fine-crystalline precipitate of 7β-amino-3-cephem-4-carboxylic acid is isolated by filtration.

Workup

  1. customevaporated to dryness in vacuo
  2. dissolutionThe residue is dissolved in a mixture of 150 ml of methanol, 250 ml of ether and 10 ml of water
  3. temperatureThe suspension is cooled for 1 hour to 0° C.

Sources & evidence

ORD record
ord-10cdf4d270bb4d59bbbc112bacac6939
Source dataset
uspto-grants-1984_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04436903

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes