Allyl bromide → HCID 18753626, compound

HRID 1838420Notes

Reaction equation

HRID 1838420 reaction equation
[OH-:1].[Na+].[O:3]([C:10]1[CH:15]=[CH:14][C:13]([S:16]([N:19]([CH:23]2[CH2:28][CH2:27][O:26][C:24]2=[O:25])[CH2:20][C:21]#[CH:22])(=[O:18])=[O:17])=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:29](Br)[CH:30]=[CH2:31].[Cl-].[NH4+]>O.C(O)C>[CH2:29]([O:25][C:24](=[O:1])[CH:23]([CH2:28][CH2:27][OH:26])[N:19]([S:16]([C:13]1[CH:14]=[CH:15][C:10]([O:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[CH:11][CH:12]=1)(=[O:17])=[O:18])[CH2:20][C:21]#[CH:22])[CH:30]=[CH2:31]

Participants

7

Reactant 4

HCID 7841Allyl bromideHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 88033492HCID 88033492, compound

Product 1

HCID 18753626HCID 18753626, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

After addition of a solution of sodium hydroxide (1.05 g, 25.5 mmol) in water (7 ml) to a suspension of (±)-α-[N-(4-phenoxybenzenesulfonyl)-N-propargylamino]-γ-butyrolactone (8.42 g, 22.7 mmol) in ethanol (40 ml), the mixture was stirred at room temperature for 3 hours. The solvent of the reaction mixture was evaporated under reduced pressure. The residue, which was an amorphous solid, was dissolved in N,N-dimethylformamide (40 ml). After addition of allyl bromide (2.15 ml, 25.4 mmol) to the solution, the mixture was stirred at room temperature overnight. A saturated aqueous solution of ammonium chloride and water were added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by chyromatography on a silica gel column using hexane/ethyl acetate=3/1 as the eluant to give the desired compound (8.29 g, yield 85%) as a pale yellow oil.

Workup

  1. customThe solvent of the reaction mixture was evaporated under reduced pressure
  2. dissolutionwas dissolved in N,N-dimethylformamide (40 ml)
  3. stirringthe mixture was stirred at room temperature overnight
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by chyromatography on a silica gel column

Sources & evidence

ORD record
ord-7240a94e4a574498816724f383cd8371
Source dataset
uspto-grants-2004_01
Patent number
US06673804B1

Reaction notes

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