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

HRID 403954

反応式

HRID 403954 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-efc7154324b44a98a9ea05ea0f974348
出典データセット
uspto-grants-2014_06
特許番号
US08748426B2

関連ノート

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