Sodium Iodide → HCID 10479059, compound

HRID 441173Notes

Reaction equation

HRID 441173 reaction equation
[Si:1]([O:8][CH:9]([C:19]([F:22])([F:21])[F:20])[CH:10]([NH:14][C:15](=[O:18])[CH2:16]Cl)[CH:11]([CH3:13])[CH3:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Na+].[I-:24].S([O-])([O-])(=O)=S.[Na+].[Na+]>CC(C)=O.O>[Si:1]([O:8][CH:9]([C:19]([F:22])([F:21])[F:20])[CH:10]([NH:14][C:15](=[O:18])[CH2:16][I:24])[CH:11]([CH3:13])[CH3:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 24477Sodium ThiosulfateHCID 10383993HCID 10383993, compound

Product 1

HCID 10479059HCID 10479059, compoundYield 91.9%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

N-(2-tert-Butyldimethylsilyloxy-3,3,3-trifluoro-1-isopropylpropyl)-2-chloroacetamide (15.56 g) was added to a solution of NaI (19.3 g) in acetone (130 mL). The mixture was stirred overnight and the yellow reaction mixture was diluted with water (180 mL). The resulting precipitate was filtered; washed with water and saturated aqueous sodium thiosulfate; and dried under vacuum at 40° C. overnight. After spectral data indicated the presence of starting material, the product was subjected to another iteration of the above reaction conditions. The subsequent work-up was identical except that no sodium thiosulfate wash was performed. Purification by chromatography, eluting with hexane:ethyl acetate (gradient, 80:20 and 50:50), and drying under vacuum afforded N-(2-tert-butyldimethylsilyloxy-3,3,3-trifluoro-1-isopropylpropyl)-2-iodoacetamide (17.91 g); TLC: Rf =0.30, hexane:ethyl acetate (9:1); MS: m/z=454(M+1).

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with water and saturated aqueous sodium thiosulfate
  3. customand dried under vacuum at 40° C. overnight
  4. customthe product was subjected to another iteration of the above reaction conditions
  5. washwash
  6. customPurification by chromatography
  7. washeluting with hexane
  8. dry with materialethyl acetate (gradient, 80:20 and 50:50), and drying under vacuum

Sources & evidence

ORD record
ord-93d3214eb2d14ebdb43b014293f7912f
Source dataset
uspto-grants-1996_05
Patent number
US05521179

Reaction notes

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