Anisole → HCID 23144325, compound

HRID 1361787Notes

Reaction equation

HRID 1361787 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:7]=[C:8]([NH:17][C:18]([C:20]2[CH:25]=[CH:24][N:23]=[C:22]([O:26]CC3C=CC(OC)=CC=3)[CH:21]=2)=[O:19])[S:9][C:10]=1[C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1.C1(OC)C=CC=CC=1.C(=O)([O-])O.[Na+]>FC(F)(F)C(O)=O>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:7]=[C:8]([NH:17][C:18]([C:20]2[CH:25]=[CH:24][NH:23][C:22](=[O:26])[CH:21]=2)=[O:19])[S:9][C:10]=1[C:11]1[CH:12]=[CH:13][N:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 7519AnisoleHCID 516892Sodium BicarbonateHCID 23144506HCID 23144506, compound

Product 1

HCID 23144325HCID 23144325, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
65 °C

Procedure

Compound 106 (2.10 g, 4.33 mmol) and anisole (4.72 mL, 43.4 mmol) were suspended in trifluoroacetic acid (7 mL), followed by stirring at 65° C. for 30 minutes. A saturated aqueous solution of sodium hydrogencarbonate was added to the reaction mixture to adjust the pH to 8, and the precipitated solid was collected by filtration. The resulting solid was purified through silica gel column chromatography (chloroform:methanol=4:1) to afford the entitled Compound 112 (1.07 g, 68%).

Workup

  1. filtrationthe precipitated solid was collected by filtration
  2. customThe resulting solid was purified through silica gel column chromatography (chloroform:methanol=4:1)

Sources & evidence

ORD record
ord-45076c5a86d04f73a4b3596f770f05f9
Source dataset
uspto-grants-2011_02
Patent number
US07880013B2

Reaction notes

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