Propargyl bromide → HCID 22644900, compound

HRID 2084891Notes

Reaction equation

HRID 2084891 reaction equation
[C:1]([O:5][NH:6][C:7](=[O:31])[CH:8]([NH:16][S:17]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]#[C:29][CH3:30])=[CH:22][CH:21]=1)(=[O:19])=[O:18])[C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].[CH2:38](Br)[C:39]#[CH:40]>CN(C=O)C>[C:1]([O:5][NH:6][C:7](=[O:31])[CH:8]([NH:16][S:17]([C:20]1[CH:21]=[CH:22][C:23]([O:26][CH2:27][C:28]#[C:29][CH3:30])=[CH:24][CH:25]=1)(=[O:19])=[O:18])[C:9]1[CH:10]=[CH:11][C:12]([O:15][CH2:40][C:39]#[CH:38])=[CH:13][CH:14]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 22644754HCID 22644754, compound

Product 1

HCID 22644900HCID 22644900, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 321.6 mg (0.72 mmol) of ′N-(tert-butoxy)-2-({[4-(2-butynyloxy)phenyl]sulfonyl}amino)-2-(4-hydroxyphenyl)acetamide from Example 176 in 3 ml DMF at 0° C. was added 199 mg (1.44 mmol) of K2CO3. The reaction mixture was stirred for 15 min, 94.4 mg (0.79 mmol) of propargyl bromide was added, and reaction mixture was stirred at room temperature overnight. DMF was removed in vacuo. The residue was diluted with ethyl acetate, washed with 1N HCl solution, water and brine. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The crude material was chromatographed on silica gel, eluting with hexane/ethyl acetate (5:1, 4:1 then 3:1) to provide 75 mg (17%) of ′N-(tert-butoxy)-2-({[4-(2-butynyloxy)phenyl]sulfonyl}amino)-2-[4-(2-propynyloxy)phenyl]acetamide as a white solid. Electrospray Mass Spec 485.4 (M+H)+.

Workup

  1. customreaction mixture
  2. stirringwas stirred at room temperature overnight
  3. customDMF was removed in vacuo
  4. additionThe residue was diluted with ethyl acetate
  5. washwashed with 1N HCl solution, water and brine
  6. dry with materialThe organic layer was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude material was chromatographed on silica gel
  10. washeluting with hexane/ethyl acetate (5:1, 4:1

Sources & evidence

ORD record
ord-25cf87525e1b420c9d209fed1bb922be
Source dataset
uspto-grants-2004_04
Patent number
US06716833B2

Reaction notes

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