Water → HCID 23114314, compound

HRID 1787316Notes

Reaction equation

HRID 1787316 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[CH:7]=[C:8]([CH:12]2[C:16]3[C:17]([CH3:31])=[C:18]([NH:23][C:24](=[O:30])[CH2:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C:19]([CH3:22])=[C:20]([CH3:21])[C:15]=3[O:14][CH2:13]2)[CH:9]=[CH:10][CH:11]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH+]1C=CC=CC=1.O>CC(C)=O.C(OCC)(=O)C>[CH:2]([C:6]1[CH:7]=[C:8]([CH:12]2[C:16]3[C:17]([CH3:31])=[C:18]([NH:23][C:24](=[O:30])[CH2:25][C:26]([CH3:27])([CH3:28])[CH3:29])[C:19]([CH3:22])=[C:20]([CH3:21])[C:15]=3[O:14][CH2:13]2)[CH:9]=[CH:10][CH:11]=1)=[O:1]

Participants

6

Reactant 3

HCID 962WaterHCID 22033616Pyridinium.p-toluenesulfonateHCID 23114090HCID 23114090, compound

Product 1

HCID 23114314HCID 23114314, compoundYield 96.1%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixed solution of N-(3-(3-(1,3-dioxolan-2-yl)phenyl)-4,6,7-trimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide (910 mg, 2.15 mmol) obtained in Example 73 and pyridinium p-toluenesulfonic acid (25 mg) in acetone (20 mL)-water (1.5 mL) was refluxed with heating for 30 minutes. The reaction solution was diluted with ethyl acetate, washed with an aqueous saturated sodium hydrogen carbonate solution, dried over anhydrous sodium sulfate, filtered, and then concentrated under reduced pressure to obtain 784 mg (yield: 96%) of the title compound. Melting point: 178-179° C. (ethyl acetate-hexane).

Workup

  1. temperaturewith heating for 30 minutes
  2. washwashed with an aqueous saturated sodium hydrogen carbonate solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0130ad8cbdc647e38c790ac2ea76dc80
Source dataset
uspto-grants-2009_03
Patent number
US07507841B2

Reaction notes

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