Propanoyl chloride, 2-(4-bromophenyl)- → (4R,5S)-3-[2-(4-Bromo-phenyl)-propionyl]-4-methyl-5-phenyl-oxazolidin-2-one

HRID 553731ノート

反応式

HRID 553731 の反応式
[CH3:1][C@@H:2]1[C@H:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[O:5][C:4](=[O:13])[NH:3]1.C([Li])CCC.[Br:19][C:20]1[CH:25]=[CH:24][C:23]([CH:26]([CH3:30])[C:27](Cl)=[O:28])=[CH:22][CH:21]=1>O1CCCC1>[Br:19][C:20]1[CH:21]=[CH:22][C:23]([CH:26]([CH3:30])[C:27]([N:3]2[C@H:2]([CH3:1])[C@H:6]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[O:5][C:4]2=[O:13])=[O:28])=[CH:24][CH:25]=1

参加物

5

反応物 3

HCID 569060Propanoyl chloride, 2-(4-bromophenyl)-HCID 2733812(4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinoneHCID 178418339Butyllithium

生成物 1

HCID 58539632(4R,5S)-3-[2-(4-Bromo-phenyl)-propionyl]-4-methyl-5-phenyl-oxazolidin-2-one

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

(4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinone (0.348 g, 1.96 mmol) was dissolved in tetrahydrofuran (20 mL) and cooled to −78° C. n-Butyllithium (1.6M in hexanes; 1.64 mL, 2.62 mmol) was added, and the reaction was stirred for 1 hour at −78° C. 2-(4-Bromo-phenyl)-propionyl chloride (0.540 g, 2.18 mmol) in tetrahydrofuran (10 mL) was added, and the reaction was stirred for 30 minutes. The mixture was concentrated, and the residue was partitioned between EtOAc and water. The organic layer was separated, dried, and concentrated, and the crude material was purified by silica gel chromatography (0-25% EtOAc in hexanes) to give two diastereomers as separated products. Diastereomer A was the first product to come off the column, while Diastereomer B was the second product to come off the column.

後処理

  1. additionwas added
  2. stirringthe reaction was stirred for 30 minutes
  3. concentrationThe mixture was concentrated
  4. customthe residue was partitioned between EtOAc and water
  5. customThe organic layer was separated
  6. customdried
  7. concentrationconcentrated
  8. customthe crude material was purified by silica gel chromatography (0-25% EtOAc in hexanes)
  9. customto give two diastereomers
  10. customas separated products

出典と根拠

ORDレコード
ord-d66cb5c08bcd4c96abc9bfc39151d3af
出典データセット
uspto-grants-2011_11
特許番号
US08048902B2

反応ノート

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