Bromide ion → HCID 18612902, compound

HRID 1264615Notes

Reaction equation

HRID 1264615 reaction equation
Br[CH2:2][C:3]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:4]=1[N+:10]([O-:12])=[O:11].[CH2:13]([O:17][C:18]1[CH:23]=[CH:22][C:21]([S:24]([NH:27][CH:28]([CH2:33][OH:34])[C:29]([O:31][CH3:32])=[O:30])(=[O:26])=[O:25])=[CH:20][CH:19]=1)C#CC.[H-].[Na+].[Br-]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O>[F:9][C:7]1[CH:6]=[CH:5][C:4]([N+:10]([O-:12])=[O:11])=[C:3]([CH:8]=1)[CH2:2][N:27]([S:24]([C:21]1[CH:20]=[CH:19][C:18]([O:17][CH3:13])=[CH:23][CH:22]=1)(=[O:26])=[O:25])[CH:28]([CH2:33][OH:34])[C:29]([O:31][CH3:32])=[O:30]

Participants

7

Reactant 4

HCID 259Bromide ionHCID 24758Sodium hydrideHCID 105616432-(Bromomethyl)-4-fluoro-1-nitrobenzeneHCID 12016494N-[[4-(2-Butyn-1-yloxy)phenyl]sulfonyl]serine methyl ester

Product 1

HCID 18612902HCID 18612902, compoundYield 84.1%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution was of 2-(bromomethyl)-4-fluoro-1-nitrobenzene (1.3 g, 5.56 mmol) at 0° C. was added tetrabutylammonium iodide (2.05 g, 5.56 mmol). The solution was stirred at 0° C. for 1.5 hours. In a separate flask, methyl 2-({[4-(2-butynyloxy)phenyl]sulfonyl}amino)-3-hydroxypropanoate (1.73 g, 5.05 mmol) was dissolved in dimethylformamide and cooled to 0° C. Sodium hydride (0.21 g, 5.56 mmol, 60% dispersion in oil) was added and the reaction was allowed to stir at 0° C. for 0.5 hours at which time the solution of the bromide was added. The reaction was stirred overnight and then quenched with water. The mixture was extracted twice with ethyl acetate, washed with brine, dried over Na2SO4, concentrated in vacuo and chromatographed using 1.5:1 hexane:ethyl acetate as eluant to provide 1.88 g (77%) of the desired product as a white solid. mp 83-88° C. Anal Calc'd for C21H21N2O8FS: C, 52.50; H, 4.41; N, 5.83. Found: C, 52.44; H, 4.76; N, 5.56.

Workup

  1. temperaturecooled to 0° C
  2. additionwas added
  3. stirringThe reaction was stirred overnight
  4. customquenched with water
  5. extractionThe mixture was extracted twice with ethyl acetate
  6. washwashed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. customchromatographed

Sources & evidence

ORD record
ord-aa94157ae0814b4e88941edb88c54668
Source dataset
uspto-grants-2003_04
Patent number
US06544984B1

Reaction notes

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