Diethyl Ether → HCID 131713208, compound

HRID 905473Notes

Reaction equation

HRID 905473 reaction equation
[NH2:1][C:2]1[S:6][N:5]=[C:4]([C:7](=[N:38][O:39][CH3:40])[C:8]([NH:10][CH:11]2[C:36](=[O:37])[N:13]3[C:14]([C:20]([O:22]C(C4C=CC=CC=4)C4C=CC=CC=4)=[O:21])=[C:15]([CH:18]=[CH2:19])[CH2:16][S:17][C@H:12]23)=[O:9])[N:3]=1.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O.C(OCC)C>C(Cl)Cl>[NH2:1][C:2]1[S:6][N:5]=[C:4]([C:7](=[N:38][O:39][CH3:40])[C:8]([NH:10][CH:11]2[C:36](=[O:37])[N:13]3[C:14]([C:20]([OH:22])=[O:21])=[C:15]([CH:18]=[CH2:19])[CH2:16][S:17][C@H:12]23)=[O:9])[N:3]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 131713209HCID 131713209, compound

Product 1

HCID 131713208HCID 131713208, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of benzhydryl 7-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyiminoacetamido]-3-vinyl-3-cephem-4-carboxylate (syn isomer) (6.2 g) in methylene chloride (60 ml) were added anisole (9.3 g) and trifluoroacetic acid (24.5 g), and the mixture was stirred at ambient temperature for 1.5 hours. After removal of the solvent, the residue was added dropwise to diisopropyl ether (600 ml), and the precipitated substance was collected by filtration. This substance was suspended in water (50 ml) and then adjusted to pH 7.5 with 2 N aqueous sodium hydroxide, followed by washing twice with a mixture of ethyl acetate (50 ml) and tetrahydrofuran (50 ml). To the resultant aqueous solution were added ethyl acetate (50 ml) and tetrahydrofuran (50 ml), and the mixture was saturated with sodium chloride and adjusted to pH 1.0 with 10% hydrochloric acid. The organic layer was separated, and the remaining aqueous solution was extracted twice with a mixture of ethyl acetate and tetrahydrofuran. The combined organic solution was washed with an aqueous sodium chloride and then dried over magnesium sulfate. Removal of the solvent gave a residue, which was pulverized with diethyl ether to obtain 7-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyiminoacetamido]-3-vinyl-3-cephem-4-carboxylic acid (syn isomer) (3.9 g).

Workup

  1. customAfter removal of the solvent
  2. additionthe residue was added dropwise to diisopropyl ether (600 ml)
  3. filtrationthe precipitated substance was collected by filtration
  4. washby washing twice with a mixture of ethyl acetate (50 ml) and tetrahydrofuran (50 ml)
  5. additionTo the resultant aqueous solution were added ethyl acetate (50 ml) and tetrahydrofuran (50 ml)
  6. customThe organic layer was separated
  7. extractionthe remaining aqueous solution was extracted twice with a mixture of ethyl acetate and tetrahydrofuran
  8. washThe combined organic solution was washed with an aqueous sodium chloride
  9. dry with materialdried over magnesium sulfate
  10. customRemoval of the solvent
  11. customgave a residue, which

Sources & evidence

ORD record
ord-5ac4f295bb644715b8d5aa41c48d311c
Source dataset
uspto-grants-1983_12
Patent number
US04423213

Reaction notes

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