Methoxyacetyl chloride → 3-[4-(2-Methoxyacetylamino)-1,3-dioxoisoindolin-2-yl]-2,6-dioxo-5-acetoxypiperidine

HRID 1883592Notes

Reaction equation

HRID 1883592 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:24])[N:5]([CH:12]1[CH2:17][CH:16]([O:18][C:19](=[O:21])[CH3:20])[C:15](=[O:22])[NH:14][C:13]1=[O:23])[C:6]2=[O:11].[CH3:25][O:26][CH2:27][C:28](Cl)=[O:29]>O1CCCC1>[CH3:25][O:26][CH2:27][C:28]([NH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:24])[N:5]([CH:12]1[CH2:17][CH:16]([O:18][C:19](=[O:21])[CH3:20])[C:15](=[O:22])[NH:14][C:13]1=[O:23])[C:6]2=[O:11])=[O:29]

Participants

4

Reactant 2

HCID 96623Methoxyacetyl chlorideHCID 222411893-(4-Amino-1,3-dioxoisoindolin-2-yl)-2,6-dioxo-5-acetoxypiperidine

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-(4-amino-1,3-dioxoisoindolin-2-yl)-2,6-dioxo-5-acetoxypiperidine (1 g, 3.5 mmol) and methoxyacetyl chloride (0.38 g, 3.5 mmol) in tetrahydrofuran (20 mL) is heated at reflux for 1 hour. The solvent is removed in vacuo to give 3-[4-(2-methoxyacetylamino)-1,3-dioxoisoindolin-2-yl]-2,6-dioxo-5-acetoxypiperidine which is further purified by column chromatography.

Workup

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

Sources & evidence

ORD record
ord-8fd763199e9b4016bccdfca451feb37a
Source dataset
uspto-grants-2004_07
Patent number
US06762195B2

Reaction notes

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