p-Toluenesulfonic acid → HCID 22241183, compound

HRID 891995Notes

Reaction equation

HRID 891995 reaction equation
[CH3:1][O:2][CH2:3][C:4]([NH:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[C:9](=[O:29])[N:10]([CH:17]1[CH2:22][CH:21]([O:23]C(=O)C)[C:20](=[O:27])[NH:19][C:18]1=[O:28])[C:11]2=[O:16])=[O:5].C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH3:1][O:2][CH2:3][C:4]([NH:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[C:9](=[O:29])[N:10]([CH:17]1[CH2:22][CH:21]([OH:23])[C:20](=[O:27])[NH:19][C:18]1=[O:28])[C:11]2=[O:16])=[O:5]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 222411983-[4-(2-Methoxyacetylamino)-1,3-dioxoisoindolin-2-yl]-2,6-dioxo-5-acetoxypiperidine

Product 1

HCID 22241183HCID 22241183, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-[4-methoxyacetylamino-1,3-dioxoisoindolin-2-yl]-2,6-dioxo-5-acetoxypiperidine (1.26 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-methoxyacetylamino-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-0ce5ec5e3ced403aac41a4b7ec1cd9f2
Source dataset
uspto-grants-2006_02
Patent number
US07005438B2

Reaction notes

Loading…