Trifluoroacetic acid → HCID 131714955, compound

HRID 1731692Notes

Reaction equation

HRID 1731692 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:46][O:47][CH3:48])[C:8]([NH:10][CH:11]2[C:44](=[O:45])[N:13]3[C:14]([C:28]([O:30]C(C4C=CC=CC=4)C4C=CC=CC=4)=[O:29])=[C:15]([CH2:18][S:19]/[CH:20]=[CH:21]\[C:22]4[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.FC(F)(F)C(O)=O>C1(OC)C=CC=CC=1>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:46][O:47][CH3:48])[C:8]([NH:10][CH:11]2[C:44](=[O:45])[N:13]3[C:14]([C:28]([OH:30])=[O:29])=[C:15]([CH2:18][S:19]/[CH:20]=[CH:21]\[C:22]4[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131714956HCID 131714956, compound

Product 1

HCID 131714955HCID 131714955, compoundYield 43.3%

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

To a suspension of benzhydryl 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-[(Z)-2-(3-pyridyl)vinylthiomethyl]-3-cephem-4-carboxylate (syn isomer) (1 g) in anisole (2.5 ml) was added trifluoroacetic acid (6 ml) under ice-cooling. The mixture was stirred for 40 minutes at ambient temperature, concentrated in vacuo to about a half volume and poured into diisopropyl ether (120 ml). The resulting precipitate was collected, dissolved in an aqueous solution (150 ml) of sodium bicarbonate (320 mg). The aqueous solution was washed with ethyl acetate and adjusted to pH 4-5 with 1N hydrochloric acid to give a precipitate. The precipitate was collected, washed with water and dried over phosphorus pentoxide to give 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-[(Z)-2-(3-pyridyl)vinylthiomethyl]-3-cephem-4-carboxylic acid (syn isomer) (330 mg).

Workup

  1. temperaturecooling
  2. concentrationconcentrated in vacuo to about a half volume
  3. additionpoured into diisopropyl ether (120 ml)
  4. customThe resulting precipitate was collected
  5. dissolutiondissolved in an aqueous solution (150 ml) of sodium bicarbonate (320 mg)
  6. washThe aqueous solution was washed with ethyl acetate
  7. customto give a precipitate
  8. customThe precipitate was collected
  9. washwashed with water
  10. dry with materialdried over phosphorus pentoxide

Sources & evidence

ORD record
ord-401ca6d772ed405ba382b23f9dcc9f9c
Source dataset
uspto-grants-1986_11
Patent number
US04622318

Reaction notes

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