Triethylamine → Methyl 2-(5-bromo-1,3-dioxoisoindolin-2-yl)-3-methylbutanoate

HRID 404122Notes

Reaction equation

HRID 404122 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])O[C:5]2=[O:12].[CH3:13][O:14][C:15](=[O:21])[C@H:16]([CH:18]([CH3:20])[CH3:19])[NH2:17].C(N(CC)CC)C>C(#N)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[N:17]([CH:16]([CH:18]([CH3:20])[CH3:19])[C:15]([O:14][CH3:13])=[O:21])[C:5]2=[O:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 665904-Bromophthalic anhydrideHCID 94285Valine methyl ester

Product 1

HCID 67305870Methyl 2-(5-bromo-1,3-dioxoisoindolin-2-yl)-3-methylbutanoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

5-bromoisobenzofuran-1,3-dione (3 g, 13.21 mmol), L-valine methyl ester (3.31 g, 19.82 mmol) and triethyl amine (2.75 mL, 19.82 mmol) were taken in acetonitrile and heated at 80° C. for 24 h. The solvent was removed by distillation and the crude material obtained was purified using column chromatography (silicagel, 20% dichloromethane in petroleum ether) to afford the title compound.

Workup

  1. customThe solvent was removed by distillation
  2. customthe crude material obtained
  3. customwas purified

Sources & evidence

ORD record
ord-872dd57215dd41e2afff162273f811f2
Source dataset
uspto-grants-2014_06
Patent number
US08748426B2

Reaction notes

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