Potassium Fluoride → (5S)-5-{[(4-Ethynyl-3,6-dihydropyridin-1(2H)-yl)sulfonyl]methyl}-5-methylimidazolidine-2,4-dione

HRID 1669654Notes

Reaction equation

HRID 1669654 reaction equation
[CH3:1][C@:2]1([CH2:9][S:10]([N:13]2[CH2:18][CH:17]=[C:16]([C:19]#[C:20][Si](C)(C)C)[CH2:15][CH2:14]2)(=[O:12])=[O:11])[NH:6][C:5](=[O:7])[NH:4][C:3]1=[O:8].[F-].[K+]>CO>[C:19]([C:16]1[CH2:17][CH2:18][N:13]([S:10]([CH2:9][C@@:2]2([CH3:1])[NH:6][C:5](=[O:7])[NH:4][C:3]2=[O:8])(=[O:12])=[O:11])[CH2:14][CH:15]=1)#[CH:20]

Participants

4

Reactant 2

HCID 522689Potassium FluorideHCID 67351634(5S)-5-Methyl-5-({[4-[(trimethylsilyl)ethynyl]-3,6-dihydropyridin-1(2H)-yl]sulfonyl}methyl)imidazolidine-2,4-dione

Product 1

HCID 86642354(5S)-5-{[(4-Ethynyl-3,6-dihydropyridin-1(2H)-yl)sulfonyl]methyl}-5-methylimidazolidine-2,4-dioneYield 101.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(5S)-5-Methyl-5-({[4-[(trimethylsilyl)ethynyl]-3,6-dihydropyridin-1(2H) -yl]sulfonyl}methyl)imidazolidine-2,4-dione (2.27 g, 6.0 mmol) and potassium fluoride (1.07 g, 18.4 mmol) were stirred overnight at room temperature in methanol (50 mL). The solvent was evaporated off, the residue dissolved in EtOAc, washed with water followed by brine, dried (sodium sulphate) and evaporated. The residue was purified by column chromatography eluting with iso-hexane/EtOAc 1:1 to give a solid product (1.81 g).

Workup

  1. customThe solvent was evaporated off
  2. dissolutionthe residue dissolved in EtOAc
  3. washwashed with water
  4. dry with materialdried (sodium sulphate)
  5. customevaporated
  6. customThe residue was purified by column chromatography
  7. washeluting with iso-hexane/EtOAc 1:1

Sources & evidence

ORD record
ord-038dc48a57cb45d3b34ee99b05e3fd28
Source dataset
uspto-grants-2011_08
Patent number
US07989620B2

Reaction notes

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