Triethylamine → (R)-Methyl 2-(5-bromo-1-oxoisoindolin-2-yl)-3-methylbutanoate

HRID 403954

Reaction equation

HRID 403954 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=O)=[C:4]([CH2:12]Br)[CH:3]=1.Cl.[CH3:15][O:16][C:17](=[O:23])[C@@H:18]([CH:20]([CH3:22])[CH3:21])[NH2:19].C(N(CC)CC)C>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:10][CH:11]=1)[C:6](=[O:8])[N:19]([C@H:18]([CH:20]([CH3:22])[CH3:21])[C:17]([O:16][CH3:15])=[O:23])[CH2:12]2

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 11984198Methyl D-valinate hydrochlorideHCID 22031079Methyl 4-bromo-2-(bromomethyl)benzoate

Product 1

HCID 86673568(R)-Methyl 2-(5-bromo-1-oxoisoindolin-2-yl)-3-methylbutanoate

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 4-bromo-2-(bromomethyl)benzoate (650 mg, 2.12 mmol) and D-valine methyl ester hydrochloride (527 mg, 3.15 mmol) was taken in toluene (6.5 mL) and to this reaction mixture, triethyl amine (428 mg, 4.24 mmol) was added and refluxed for about 16 h. After completion of the reaction, the reaction mixture was diluted with ethyl acetate and washed with water and brine, dried over anhydrous sodium sulfate and concentrated to obtain an oil, which was purified by column chromatography (silica gel, 30% ethyl acetate in petroleum ether) to obtain the title compound.

Workup

  1. additionwas added
  2. temperaturerefluxed for about 16 h
  3. customAfter completion of the reaction
  4. washwashed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customto obtain an oil, which
  8. customwas purified by column chromatography (silica gel, 30% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-efc7154324b44a98a9ea05ea0f974348
Source dataset
uspto-grants-2014_06
Patent number
US08748426B2

Linked notes

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