Allyl bromide → HCID 22180553, compound

HRID 1796765Notes

Reaction equation

HRID 1796765 reaction equation
[CH:1]1([N:7]2[CH2:15][C:14]3[C:9](=[CH:10][C:11]([N:16]4[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][CH2:24][CH2:25][C:26]5([C:39](=[O:46])[NH:40][CH2:41][C:42]([F:45])([F:44])[F:43])[C:38]6[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=6[C:32]6[C:27]5=[CH:28][CH:29]=[CH:30][CH:31]=6)[CH2:18][CH2:17]4)=[CH:12][CH:13]=3)[C:8]2=[O:47])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].C(=O)([O-])[O-].[K+].[K+].[CH2:56](Br)[CH:57]=[CH2:58]>C1(C)C=CC=CC=1.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH:1]1([N:7]2[CH2:15][C:14]3[C:9](=[CH:10][C:11]([N:16]4[CH2:17][CH2:18][N:19]([CH2:22][CH2:23][CH2:24][CH2:25][C:26]5([C:39](=[O:46])[NH:40][CH:41]([CH2:58][CH:57]=[CH2:56])[C:42]([F:45])([F:43])[F:44])[C:38]6[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=6[C:32]6[C:27]5=[CH:28][CH:29]=[CH:30][CH:31]=6)[CH2:20][CH2:21]4)=[CH:12][CH:13]=3)[C:8]2=[O:47])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

8

Reactant 4

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 22180255HCID 22180255, compound

Product 1

HCID 22180553HCID 22180553, compoundYield 16.5%

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

The compound (0.100 g) prepared in Example 92 was dissolved in toluene (5 ml). Sodium hydroxide (0.019 g), potassium carbonate (0.041 g), tetrabutylammonium hydrogen sulfate (0.012 g), and allyl bromide (0.015 ml) were added to the solution, and the mixture was stirred at 60° C. overnight. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was then removed by distillation under the reduced pressure. The residue was purified by preparative TLC (hexane:ethyl acetate=1:3) to give the title compound (0.017 g, 16.5%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was then removed by distillation under the reduced pressure
  4. customThe residue was purified by preparative TLC (hexane:ethyl acetate=1:3)

Sources & evidence

ORD record
ord-8628682b5b494940a07e8c68e5683ccd
Source dataset
uspto-grants-2006_04
Patent number
US07030120B2

Reaction notes

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