Allyl bromide → HCID 9853167, compound

HRID 1836828Notes

Reaction equation

HRID 1836828 reaction equation
[CH2:1]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([N:18]3[CH2:23][CH2:22][N:21]([CH2:24][CH2:25][CH2:26][CH2:27][C:28]4([C:41](=[O:48])[NH:42][CH2:43][C:44]([F:47])([F:46])[F:45])[C:40]5[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=5[C:34]5[C:29]4=[CH:30][CH:31]=[CH:32][CH:33]=5)[CH2:20][CH2:19]3)=[CH:13][CH:14]=2)[C:9]1=[O:49])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].C(=O)([O-])[O-].[K+].[K+].[CH2:58](Br)[CH:59]=[CH2:60]>C1(C)C=CC=CC=1.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH2:60]([N:42]([CH2:43][C:44]([F:45])([F:46])[F:47])[C:41]([C:28]1([CH2:27][CH2:26][CH2:25][CH2:24][N:21]2[CH2:22][CH2:23][N:18]([C:12]3[CH:11]=[C:10]4[C:15]([CH2:16][CH2:17][N:8]([CH2:1][C:2]5[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=5)[C:9]4=[O:49])=[CH:14][CH:13]=3)[CH2:19][CH2:20]2)[C:40]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[C:34]2[C:29]1=[CH:30][CH:31]=[CH:32][CH:33]=2)=[O:48])[CH:59]=[CH2:58]

Participants

8

Reactant 4

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 22180517HCID 22180517, compound

Product 1

HCID 9853167HCID 9853167, compound

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

The compound (67 mg) prepared in Example 97 was dissolved in toluene (5 ml), and sodium hydroxide (12 mg), potassium carbonate (28 mg), tetrabutylammonium hydrogensulfate (8 mg), and allyl bromide (0.010 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 extract was dried over anhydrous MgSO4, and the solvent was then removed by distillation under the reduced pressure. The residue was purified by preparative TLC (hexane:ethyl acetate=1:1) to give the title compound (17 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous MgSO4
  3. customthe solvent was then removed by distillation under the reduced pressure
  4. customThe residue was purified by preparative TLC (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-e763611b2f3742f3845d1579cd9648d9
Source dataset
uspto-grants-2004_08
Patent number
US06777414B1

Reaction notes

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