Sodium Carbonate → HCID 22054324, compound

HRID 1830258Notes

Reaction equation

HRID 1830258 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH3:31])=[C:5]([C:22]([O:29][CH3:30])=[C:23]([O:27][CH3:28])[C:24]=1[O:25][CH3:26])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([OH:21])=[C:11]([CH:20]=1)[C:12]([N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1)=[O:13].C(=O)([O-])[O-].[Na+].[Na+].Br[CH2:39][C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41]>CC(C)=O>[CH3:1][O:2][C:3]1[C:4]([CH3:31])=[C:5]([C:22]([O:29][CH3:30])=[C:23]([O:27][CH3:28])[C:24]=1[O:25][CH3:26])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:21][CH2:39][C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])=[C:11]([CH:20]=1)[C:12]([N:14]1[CH2:15][CH2:16][O:17][CH2:18][CH2:19]1)=[O:13]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 79177tert-Butyl bromoacetateHCID 22054155HCID 22054155, compound

Product 1

HCID 22054324HCID 22054324, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

N-[5-(3,4,5,6-Tetramethoxy-2-methylbenzyl)-2-hydroxybenzoyl]morpholine (0.200 g, 0.465 mmol) was dissolved in acetone (30 ml) and after adding thereto anhydrous sodium carbonate (0.077 g, 0.558 mmol) and tert-butyl bromoacetate (0.109 g, 0.558 mol), the solution was refluxed under heating for 3 hours. The reaction solution was filtered, the filtrate was concentrated and the obtained residue was purified by silica gel column chromatography (hexand:ethyl acetate=2:1) to obtain the titled compound (0.198 g, 0.363 mmol, 78%).

Workup

  1. additionafter adding
  2. temperatureunder heating for 3 hours
  3. filtrationThe reaction solution was filtered
  4. concentrationthe filtrate was concentrated
  5. customthe obtained residue was purified by silica gel column chromatography (hexand:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-5c01afee4ff144328bc5aff3ec46d55d
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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