Sodium Iodide → HCID 131713336, compound

HRID 905459Notes

Reaction equation

HRID 905459 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:25][O:26][CH3:27])[C:8]([NH:10][CH:11]2[C:23](=[O:24])[N:13]3[C:14]([C:20]([O-:22])=[O:21])=[C:15]([CH:18]=[CH2:19])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.[Na+].[I-].[Na+].[C:31]([O:34][CH:35](Br)[CH2:36][CH3:37])(=[O:33])[CH3:32].C(OC(C)C)(C)C>CN(C)C=O.C(OCC)(=O)C.O>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:25][O:26][CH3:27])[C:8]([NH:10][CH:11]2[C:23](=[O:24])[N:13]3[C:14]([C:20]([O:22][CH:35]([O:34][C:31](=[O:33])[CH3:32])[CH2:36][CH3:37])=[O:21])=[C:15]([CH:18]=[CH2:19])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 7914Diisopropyl Ether2×HCID 157302611-Propanol, 1-bromo-, 1-acetateHCID 131713178Sodium 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-vinyl-3-cephem-4-carboxylate

Product 1

HCID 131713336HCID 131713336, compoundYield 26.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of sodium 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-vinyl-3-cephem-4-carboxylate (syn isomer)(2.0 g) in N,N-dimethylformamide (40 ml) was added sodium iodide (0.8 g) and 1-bromopropyl acetate (0.9 g) under ice-cooling with stirring, and the stirring was continued at the same temperature for half an hour. The reaction mixture was poured into a mixture of water and ethyl acetate, and the separated organic solution was washed twice with a saturated aqueous sodium chloride and twice with water, followed by drying over anhydrous magnesium sulfate. Removal of the solvent gave a residue, which was pulverized with diisopropyl ether and then chromatographed on silica gel eluting with a mixed solvent of ethyl acetate and chloroform (4:6 to 6:4 by volume), and fractions containing a desired compound were collected. Removal of the solvent gave a residue, which was pulverized with diisopropyl ether and then collected by filtration to obtain 1-acetoxypropyl 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-vinyl-3-cephem-4-carboxylate (syn isomer)(0.62 g), mp 97°-101° C.

Workup

  1. temperaturecooling
  2. waitthe stirring was continued at the same temperature for half an hour
  3. washthe separated organic solution was washed twice with a saturated aqueous sodium chloride and twice with water
  4. dry with materialby drying over anhydrous magnesium sulfate
  5. customRemoval of the solvent
  6. customgave a residue, which
  7. customchromatographed on silica gel eluting with a mixed solvent of ethyl acetate and chloroform (4:6 to 6:4 by volume), and fractions
  8. additioncontaining a desired compound
  9. customwere collected
  10. customRemoval of the solvent
  11. customgave a residue, which
  12. filtrationcollected by filtration

Sources & evidence

ORD record
ord-c8440feaf9ac49d2bed0e727b3fa9418
Source dataset
uspto-grants-1983_12
Patent number
US04423213

Reaction notes

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