Sodium Iodide → HCID 131718061, compound

HRID 2253994Notes

Reaction equation

HRID 2253994 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][C@@H:11]2[C:32](=[O:33])[N:13]3[C:14]([C:20]([O:22][CH2:23][C:24]4[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=4)=[O:21])=[C:15]([CH2:18]Cl)[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I-].[Na+].[CH:55]([C:57]1[CH:61]=[CH:60][S:59][N:58]=1)=O.C(=O)([O-])O.[Na+]>CN(C)C=O>[C:1]1([CH2:7][C:8]([NH:10][C@@H:11]2[C:32](=[O:33])[N:13]3[C:14]([C:20]([O:22][CH2:23][C:24]4[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=4)=[O:21])=[C:15]([CH:18]=[CH:55][C:57]4[CH:61]=[CH:60][S:59][N:58]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 11776TriphenylphosphineHCID 516892Sodium BicarbonateHCID 10874591(4-Methoxyphenyl)methyl (6R,7R)-3-(chloromethyl)-8-oxo-7-((2-phenylacetyl)amino)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylateHCID 13856554isothiazole-3-carbaldehyde

Product 1

HCID 131718061HCID 131718061, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 20 ml of dimethylformamide were dissolved 3.0 g (6.16 mmol) of p-methoxybenzyl 7β-phenylacetamido-3-chloromethyl-3-cephem-4carboxylate and 1.70 g (6.48 mmol) of triphenylphosphine, and 0.97 g (6.47 mmol) of sodium iodide was added therein, and the stirring was effected for 2 hrs. at the room temperature. The reaction solution was concentrated and dried under the reduced pressure and 10 ml of methylene chloride was added therein. To this solution were added 767 mg (6.78 mmol) of 3-formylisothiazole and 10 ml of saturated sodium hydrogen carbonate aqueous solution, and the stirring was effected for 5.5 hrs. at the room temperature. The layer of methylene chloride was separated, and the aqueous layer was extracted with methylene chloride. The layers of methylene chloride were combined, washed with saturated saline solution; and dried over anhydrous magnesium sulfate, and then, the solvent was evaporated off to give 6.8 g of a caramel. This caramel was column chromatographed on silica gel by eluting with chloroform-ethyl acetate to give 2.48 g of p-methoxybenzyl 7β-phenylacetamido-3-[2-(isothiazol-3-yl)vinyl]-3-cephem-4-carboxylate.

Workup

  1. additionwas added
  2. customat the room temperature
  3. concentrationThe reaction solution was concentrated
  4. dry with materialdried under the reduced pressure and 10 ml of methylene chloride
  5. additionwas added
  6. waitthe stirring was effected for 5.5 hrs
  7. customat the room temperature
  8. customThe layer of methylene chloride was separated
  9. extractionthe aqueous layer was extracted with methylene chloride
  10. washwashed with saturated saline solution
  11. dry with materialand dried over anhydrous magnesium sulfate
  12. customthe solvent was evaporated off
  13. customto give 6.8 g of a caramel
  14. customchromatographed on silica gel
  15. washby eluting with chloroform-ethyl acetate

Sources & evidence

ORD record
ord-b75692bf09ab4befbe4f8fc9e8ac7845
Source dataset
uspto-grants-1993_08
Patent number
US05233035

Reaction notes

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