p-Toluenesulfonic acid → HCID 22241202, compound

HRID 1172718Notes

Reaction equation

HRID 1172718 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([NH:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[C:11](=[O:31])[N:12]([CH:19]1[CH2:24][CH:23]([O:25]C(=O)C)[C:22](=[O:29])[NH:21][C:20]1=[O:30])[C:13]2=[O:18])=[O:7].C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([NH:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[C:11](=[O:31])[N:12]([CH:19]1[CH2:24][CH:23]([OH:25])[C:22](=[O:29])[NH:21][C:20]1=[O:30])[C:13]2=[O:18])=[O:7]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 22241181HCID 22241181, compound

Product 1

HCID 22241202HCID 22241202, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-[4-(2-furylcarbonylamino)-1,3-dioxoisoindolin-2-yl]-2,6-dioxo-5-acetoxypiperidine (1.33 g, 3.5 mmol) and p-toluenesulfonic acid (0.33 g, 1.8 mmol) in methanol (20 mL) is heated at reflux for 5 hours. The solvent is removed in vacuo to give 3-[4-(2-furylcarbonylamino)-1,3-dioxoisoindolin-2-yl]-2,6-dioxo-5-hydroxypiperidine which is further purified by column chromatography.

Workup

  1. temperatureat reflux for 5 hours
  2. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-cee0cbe364994205992816151e63d641
Source dataset
uspto-grants-2010_11
Patent number
US07834033B2

Reaction notes

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