Trifluoroacetic acid → HCID 131713203, compound

HRID 1195563Notes

Reaction equation

HRID 1195563 reaction equation
FC(F)(F)C(O)=[O:4].CN([CH:11]=[N:12][C:13]1[S:17][N:16]=[C:15]([C:18](=[N:49][O:50][CH2:51][C:52]([O:54]C(C)(C)C)=[O:53])[C:19]([NH:21][CH:22]2[C:47](=[O:48])[N:24]3[C:25]([C:31]([O:33]C(C4C=CC=CC=4)C4C=CC=CC=4)=[O:32])=[C:26]([CH:29]=[CH2:30])[CH2:27][S:28][C@H:23]23)=[O:20])[N:14]=1)C.C(OC(C)C)(C)C>C(Cl)Cl.C1(OC)C=CC=CC=1>[CH:11]([NH:12][C:13]1[S:17][N:16]=[C:15]([C:18](=[N:49][O:50][CH2:51][C:52]([OH:54])=[O:53])[C:19]([NH:21][CH:22]2[C:47](=[O:48])[N:24]3[C:25]([C:31]([OH:33])=[O:32])=[C:26]([CH:29]=[CH2:30])[CH2:27][S:28][C@H:23]23)=[O:20])[N:14]=1)=[O:4]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7914Diisopropyl EtherHCID 131713204HCID 131713204, compound

Product 1

HCID 131713203HCID 131713203, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7519AnisoleSolvent

Procedure

Trifluoroacetic acid (16.0 ml) was added to a solution of benzhydryl 7-[2-[5-{N-(N,N-dimethylaminomethylene)amino}-1,2,4-thiadiazol-3-yl]-2-tert-butoxycarbonylmethoxyiminoacetamido]-3-vinyl-3-cephem-4-carboxylate (syn isomer) (4.0 g) in methylene chloride (8.0 ml) and anisole (4.0 ml) under ice-cooling, and the mixture was stirred at ambient temperature for 1.5 hours. The reaction mixture was added dropwise to diisopropyl ether (200 ml), and the precipitated substance was collected by filtration and then added to a mixture of water and ethyl acetate, followed by adjusting to pH 7.5 with a saturated aqueous sodium bicarbonate. The separated aqueous layer was saturated with sodium chloride and adjusted to pH 2.5 with 10% hydrochloric acid, followed by extraction with a mixed solvent of ethyl acetate and tetrahydrofuran (1:2 by volume). The extract was washed with a saturated aqueous sodium chloride and then dried over magnesium sulfate. Removal of the solvent gave a residue, which was washed with diethyl ether and collected by filtration to obtain 7-[2-(5-formamido-1,2,4-thiadiazol-3-yl)-2-carboxymethoxyiminoacetamido]-3-vinyl-3-cephem-4-carboxylic acid (syn isomer) (1.75 g).

Workup

  1. temperaturecooling
  2. filtrationthe precipitated substance was collected by filtration
  3. additionadded to a mixture of water and ethyl acetate
  4. extractionfollowed by extraction with a mixed solvent of ethyl acetate and tetrahydrofuran (1:2 by volume)
  5. washThe extract was washed with a saturated aqueous sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. customRemoval of the solvent
  8. customgave a residue, which
  9. washwas washed with diethyl ether
  10. filtrationcollected by filtration

Sources & evidence

ORD record
ord-95815b22d7c64c9180b2a99c2360941a
Source dataset
uspto-grants-1992_05
Patent number
US05110921

Reaction notes

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