Trifluoroacetic acid → HCID 131712115, compound

HRID 127188Notes

Reaction equation

HRID 127188 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[CH:7]=[CH:8][C:9]1[CH2:10][S:11][C@@H:12]2[C@H:32]([NH:33][C:34](=[O:41])[CH2:35][C:36]3[S:37][CH:38]=[CH:39][CH:40]=3)[C:31](=[O:42])[N:13]2[C:14]=1[C:15]([O:17]C(C1C=CC=CC=1)C1C=CC=CC=1)=[O:16].FC(F)(F)C(O)=O>C1(OC)C=CC=CC=1>[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[CH:7]=[CH:8][C:9]1[CH2:10][S:11][C@@H:12]2[CH:32]([NH:33][C:34](=[O:41])[CH2:35][C:36]3[S:37][CH:38]=[CH:39][CH:40]=3)[C:31](=[O:42])[N:13]2[C:14]=1[C:15]([OH:17])=[O:16]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131712116HCID 131712116, compound

Product 1

HCID 131712115HCID 131712115, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

To a solution of 147 mg of benzhydryl 3-(2-pyrazinylvinyl)-7β-(2-thienylacetamido)-3-cephem-4-carboxylate in 1.5 ml anisole at 0° was added 3 ml of cold trifluoroacetic acid. The solution was kept 10 minutes at 0° and then placed directly on a vacuum pump and evaporated. The residue was flushed with 1 ml anisole and reevaporated. The residue was triturated with 4 ml boiling ether and the ether was cooled and siphoned off. This procedure was repeated twice more. The remaining insoluble material weighed 116 mg yield 87% (calculated as mono--CF3COOH salt) and was characterized by n.m.r. and electrophoresis.

Workup

  1. customevaporated
  2. customThe residue was flushed with 1 ml anisole
  3. customreevaporated
  4. customThe residue was triturated with 4 ml
  5. temperaturethe ether was cooled

Sources & evidence

ORD record
ord-9ae1eac9c0914b608bac0985bdf5c1b1
Source dataset
uspto-grants-1981_03
Patent number
US04255423

Reaction notes

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