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

HRID 1381396Notes

Reaction equation

HRID 1381396 reaction equation
C(=[N:8][CH:9]1[C:34](=[O:35])[N:11]2[C:12]([C:18]([O:20]C(C3C=CC=CC=3)C3C=CC=CC=3)=[O:19])=[C:13]([CH:16]=[CH2:17])[CH2:14][S:15][C@H:10]12)C1C=CC=CC=1.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>C1(OC)C=CC=CC=1.C(OCC)(=O)C>[NH2:8][CH:9]1[C:34](=[O:35])[N:11]2[C:12]([C:18]([OH:20])=[O:19])=[C:13]([CH:16]=[CH2:17])[CH2:14][S:15][C@H:10]12

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 516892Sodium BicarbonateHCID 12818010Benzhydryl 7-benzylideneamino-3-vinyl-3-cephem-4-carboxylate

Product 1

HCID 128180067-Amino-3vinyl-3-cephem-4-carboxylic acidYield 49.4%

Reagents, catalysts & solvents 2

HCID 7519AnisoleSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of benzhydryl 7-benzylideneamino-3-vinyl-3-cephem-4-carboxylate (8.6 g) in anisole (10 ml) was added dropwise trifluoroacetic acid (10 ml) at -20° C., and the reaction temperature was gradually raised to ambient temperature with stirring, followed by stirring at ambient temperature for half an hour. The reaction mixture was poured into a mixture of ethyl acetate (100 ml) and a saturated aqueous sodium bicarbonate (100 ml), and then the mixture was adjusted to pH 7.5 with 20% aqueous sodium carbonate. The separated aqueous solution was washed with ethyl acetate (100 ml) and adjusted to pH 7.2 with conc. hydrochloric acid, followed by subjecting to column chromatography on alumina (10 ml). Elution was carried out with 15% aqueous sodium chloride, and fractions containing a desired compound were collected and then adjusted to pH 3.3 with conc. hydrochloric acid. The precipitated crystals were collected by filtration, washed with acetone and dried to obtain 7-amino-3-vinyl-3-cephem-4-carboxylic acid (2.0 g), mp 200°-230° C. (dec.).

Workup

  1. stirringby stirring at ambient temperature for half an hour
  2. washThe separated aqueous solution was washed with ethyl acetate (100 ml)
  3. washElution
  4. additioncontaining a desired compound
  5. customwere collected
  6. filtrationThe precipitated crystals were collected by filtration
  7. washwashed with acetone
  8. customdried

Sources & evidence

ORD record
ord-02a6fa6a2cdf467db25085ec02720466
Source dataset
uspto-grants-1986_04
Patent number
US04585860

Reaction notes

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