Sodium Iodide → HCID 86752082, compound

HRID 862398Notes

Reaction equation

HRID 862398 reaction equation
[Si:1]([O:8][C@@H:9]([C@@H:11]1[C@@H:14]([CH2:15][C:16](=[O:21])/[CH:17]=[CH:18]\[O:19][CH3:20])[N:13]([CH:22](O)[C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=2)=[O:24])[C:12]1=[O:37])[CH3:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].N1C(C)=CC=CC=1C.S(Cl)(Cl)=O.[C:50]1([P:56]([C:63]2[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=2)[C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1.[I-].[Na+]>C1COCC1>[Si:1]([O:8][C@@H:9]([C@@H:11]1[C@@H:14]([CH2:15][C:16](=[O:21])/[CH:17]=[CH:18]\[O:19][CH3:20])[N:13]([C:22](=[P:56]([C:57]2[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=2)([C:63]2[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=2)[C:50]2[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=2)[C:23]([O:25][CH2:26][C:27]2[CH:28]=[CH:29][C:30]([N+:33]([O-:35])=[O:34])=[CH:31][CH:32]=2)=[O:24])[C:12]1=[O:37])[CH3:10])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 79372,6-Lutidine2×HCID 11776TriphenylphosphineHCID 24386Thionyl ChlorideHCID 86752083HCID 86752083, compound

Product 1

HCID 86752082HCID 86752082, compoundYield 60.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-nitrobenzyl 2-[(3S ,4R)-3-[(1R)-1(tert-butyldimethylsilyloxy)-ethyl]-4-[(4Z)-methoxy-2-oxobut-3-en-1-yl]-2-azetidinon-1-yl]-2-hydroxyacetate (8.49 g, 15.8 mmol) in THF (300 ml) at -20° C. was added successively 2,6-lutidine (5.5 ml, 47.5 mmol) and thionylchloride (1.7 ml, 24 mmol). The cooling bath was removed and the reaction mixture stirred at ambient temperature for 30 minutes. The mixture was filtered, the solvent evaporated, the residue redissolved in toluene, the solution again filtered and evaporated. The residue was taken up in THF (300 ml) and triphenylphosphine (8.3 g, 32 mmol), 2,6-lutidine (3.7 ml, 32 mmol) and sodium iodide (0.5 g, 32 mmol) were added successively. The reaction mixture was stirred at ambient temperature for 1 hour, filtered and evaporated. The residue was purified by flash chromatography on silica using dichloromethane/ethyl acetate (8:2) as eluant to afford the title compound 4-nitrobenzyl 2-[(3S,4R)-3[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(4Z)-methoxy-2-oxobut-3-en-1-yl]-2-azetidinon-1-yl]-2-(triphenylphosphoranylidene)acetate (7.5 g, 58% ).

Workup

  1. customThe cooling bath was removed
  2. filtrationThe mixture was filtered
  3. customthe solvent evaporated
  4. dissolutionthe residue redissolved in toluene
  5. filtrationthe solution again filtered
  6. customevaporated
  7. stirringThe reaction mixture was stirred at ambient temperature for 1 hour
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was purified by flash chromatography on silica

Sources & evidence

ORD record
ord-86e7bbd3ea264ab7a3f14097420b6425
Source dataset
uspto-grants-1998_02
Patent number
US05719139

Reaction notes

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