Trifluoroacetic acid → HCID 131713439, compound

HRID 1650926Notes

Reaction equation

HRID 1650926 reaction equation
C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O.[NH2:16][C:17]1[S:18][C:19]([Cl:48])=[C:20]([C:22](=[N:38][O:39][CH2:40][C:41]([O:43]C(C)(C)C)=[O:42])[C:23]([NH:25][CH:26]2[C:36](=[O:37])[N:28]3[C:29]([C:33]([OH:35])=[O:34])=[CH:30][CH2:31][S:32][C@H:27]23)=[O:24])[N:21]=1>CCOCC>[NH2:16][C:17]1[S:18][C:19]([Cl:48])=[C:20]([C:22](=[N:38][O:39][CH2:40][C:41]([OH:43])=[O:42])[C:23]([NH:25][CH:26]2[C:36](=[O:37])[N:28]3[C:29]([C:33]([OH:35])=[O:34])=[CH:30][CH2:31][S:32][C@H:27]23)=[O:24])[N:21]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 131713434HCID 131713434, compound

Product 1

HCID 131713439HCID 131713439, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a mixture of anisole (2 ml) and trifluoroacetic acid (6 ml) was added 7-[2-(2-amino-5-chlorothiazol-4-yl)-2-tert-butoxycarbonylmethoxyiminoacetamido]-3-cephem-4-carboxylic acid (syn isomer)(1.7 g) at 20° to 25° C. with stirring. The reaction mixture was stirred for an hour at the same temperature. The resultant solution was poured into a mixed solvent of dissopropyl ether (300 ml) and petroleum ether (100 ml). The precipitates were collected by filtration, washed with petroleum ether, and were dissolved in an aqueous solution of sodium bicarbonate at pH 7.5. The aqueous solution was washed with ethyl acetate, adjusted to pH 2.8 with a diluted hydrochloric acid, and extracted with a mixed solvent of ethyl acetate and tetrahydrofuran. The organic layer was washed with a saturated aqeous solution of sodium chloride and dried over magnesium sulfate. After removing the solvent in vacuo, diisopropyl ether was added to the residue. The insoluble precipitates were collected by filtration to give 7-[2-(2-amino-5-chlorothiazol-4-yl)-2-carboxymethoxyiminoacetamido]-3-cephem-4-carboxylic acid (syn isomer)(1.2 g), mp 165° to 167° C. (dec.).

Workup

  1. stirringThe reaction mixture was stirred for an hour at the same temperature
  2. filtrationThe precipitates were collected by filtration
  3. washwashed with petroleum ether
  4. dissolutionwere dissolved in an aqueous solution of sodium bicarbonate at pH 7.5
  5. washThe aqueous solution was washed with ethyl acetate
  6. extractionextracted with a mixed solvent of ethyl acetate and tetrahydrofuran
  7. washThe organic layer was washed with a saturated aqeous solution of sodium chloride
  8. dry with materialdried over magnesium sulfate
  9. customAfter removing the solvent in vacuo, diisopropyl ether
  10. additionwas added to the residue
  11. customThe insoluble precipitates
  12. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-2701465e880b4f01a60d393a8deb9d7c
Source dataset
uspto-grants-1990_05
Patent number
US04925948

Reaction notes

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