Sodium Iodide → HCID 131713927, compound

HRID 1632761Notes

Reaction equation

HRID 1632761 reaction equation
[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:37][O:38][CH3:39])[C:10]([NH:12][CH:13]2[C:35](=[O:36])[N:15]3[C:16]([C:21]([O:23][CH:24]([CH2:30][O:31][CH:32]([CH3:34])[CH3:33])[CH2:25][O:26][CH:27]([CH3:29])[CH3:28])=[O:22])=[CH:17][CH2:18][S:19](=O)[C@H:14]23)=[O:11])[N:8]=1)=[O:2].[I-].[Na+].FC(F)(F)C(OC(=O)C(F)(F)F)=O>CC(C)=O>[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:37][O:38][CH3:39])[C:10]([NH:12][CH:13]2[C:35](=[O:36])[N:15]3[C:16]([C:21]([O:23][CH:24]([CH2:25][O:26][CH:27]([CH3:28])[CH3:29])[CH2:30][O:31][CH:32]([CH3:33])[CH3:34])=[O:22])=[CH:17][CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1)=[O:2]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 9845Trifluoroacetic anhydrideHCID 131713925HCID 131713925, compound

Product 1

HCID 131713927HCID 131713927, compoundYield 88.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of 2-isopropoxy-1-isopropoxymethylethyl 7-[2-(2-formamidothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate-1-oxide (syn isomer, 6.5 g) and sodium iodide (5 g) in dried acetone (130 ml) was dropwise added trifluoroacetic anhydride (7 g) at -2° C. over 16 minutes, and stirred at 0° to 5° C. for 1.2 hours. The resultant mixture was poured into ice water (650 ml), and then extracted with ethyl acetate (200 ml). The extract was washed with an aqueous solution of sodium sulfite (50 ml) and a saturated aqueous solution of sodium chloride (50 ml) in turn. The solution was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was triturated with diethylether (100 ml). The precipitates were collected by filtration to give 2-isopropoxy-1-isopropoxymethylethyl 7-[2-(2-formamidothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate (syn isomer, 5.6 g).

Workup

  1. customat -2° C.
  2. customover 16 minutes
  3. extractionextracted with ethyl acetate (200 ml)
  4. washThe extract was washed with an aqueous solution of sodium sulfite (50 ml)
  5. dry with materialThe solution was dried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was triturated with diethylether (100 ml)
  8. filtrationThe precipitates were collected by filtration

Sources & evidence

ORD record
ord-b82a09b95f1544f9b0d89e46745a3a1b
Source dataset
uspto-grants-1984_10
Patent number
US04477447

Reaction notes

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