p-Toluenesulfonic acid → HCID 67180922, compound

HRID 2362244Notes

Reaction equation

HRID 2362244 reaction equation
[Br:1][C:2]1[O:6][C:5]([C:7]([CH:9]2[C:18](=[O:19])[CH2:17][CH2:16][C:11]3([O:15][CH2:14][CH2:13][O:12]3)[CH2:10]2)=[O:8])=[CH:4][CH:3]=1.NC1C=CC(C(N)=[O:26])=CC=1C.CC1C=CC(S(O)(=O)=O)=CC=1>CCO>[Br:1][C:2]1[O:6][C:5]([C:7](=[O:8])[CH2:9][CH2:10][C:11]2([CH2:16][CH2:17][C:18]([OH:19])=[O:26])[O:12][CH2:13][CH2:14][O:15]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 121180574-amino-3-methylbenzamideHCID 67179716HCID 67179716, compound

Product 1

HCID 67180922HCID 67180922, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

7-(5-bromofuran-2-carbonyl)-1,4-dioxaspiro[4.5]decan-8-one. (2.00 g, 5.78 mmol), 4-amino-3-methylbenzamide (1.04 mg, 6.90 mmol) and TsOH (100 mg, 0.578 mmol) were taken up into EtOH (20 mL). The resulted mixture was heated to reflux for 61 h. After evaporation under reduced pressure, the crude product was purified by a silica gel column chromatography (EA:PE=1:1) to afford 3-(2-(3-(5-bromofuran-2-yl)-3-oxopropyl)-1,3-dioxolan-2-yl)propanoic acid as a yellow solid (760 mg, yield: 30%).

Workup

  1. temperatureThe resulted mixture was heated
  2. temperatureto reflux for 61 h
  3. customAfter evaporation under reduced pressure
  4. customthe crude product was purified by a silica gel column chromatography (EA:PE=1:1)

Sources & evidence

ORD record
ord-7af5c305486c47e6b7168b3000b36119
Source dataset
uspto-grants-2014_04
Patent number
US08691816B2

Reaction notes

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