Pivaloyl chloride → (4R,5S)-3-[3-(2,4-Difluoro-phenyl)-propionyl]-4-methyl-5-phenyl-oxazolidin-2-one

HRID 132635

反応式

HRID 132635 の反応式
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][C:11]([OH:13])=O.CC(C)(C)C(Cl)=O.[Li+].[Cl-].[CH3:23][C@H:24]1[C@@H:28]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[O:27][C:26](=[O:35])[NH:25]1>C(N(CC)CC)C.C1COCC1>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][C:11]([N:25]1[C@H:24]([CH3:23])[C@H:28]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[O:27][C:26]1=[O:35])=[O:13]

参加物

7

反応物 4

HCID 62493Pivaloyl chlorideHCID 433294Lithium ChlorideHCID 8531614-Methyl-5-phenyl-2-oxazolidinone, (4S,5R)-HCID 49863953-(2,4-difluorophenyl)propanoic Acid

生成物 1

HCID 69267110(4R,5S)-3-[3-(2,4-Difluoro-phenyl)-propionyl]-4-methyl-5-phenyl-oxazolidin-2-one収率 99%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8471Triethylamine溶媒

反応条件

温度
0 °C

実験手順

A flask was charged with 29.5 g (158 mmol) of 3-(2,4-difluoro-phenyl)-propionic acid, 700 mL of THF, and 82.8 mL of triethylamine. The mixture was cooled to 0° C. and 23.4 mL of trimethyl acetyl chloride was added slowly. The mixture was stirred cold for 1 hour. Then 8.06 g (190 mmol) of LiCl and 28.1 g of (4S,5R)-4-methyl-5-phenyl-oxazolidin-2-one was added. The mixture was allowed to warm room temperature and stirred overnight. The solids were filtered off, and the solvent was removed under reduced pressure. The residue was taken up in diethyl ether and washed with sat. aq. ammonium chloride, sat. aq. sodium bicarbonate, and the solvent was removed under reduced pressure. The crude residue was purified by column chromatography (3:1 dichloromethane/hexanes eluent) to give 54 g (99% yield) of the titled compound.

後処理

  1. temperatureto warm room temperature
  2. stirringstirred overnight
  3. filtrationThe solids were filtered off
  4. customthe solvent was removed under reduced pressure
  5. washwashed with sat. aq. ammonium chloride, sat. aq. sodium bicarbonate
  6. customthe solvent was removed under reduced pressure
  7. customThe crude residue was purified by column chromatography (3:1 dichloromethane/hexanes eluent)

出典と根拠

ORDレコード
ord-5aab9024ad7c4aac9a0a584ae2318b23
出典データセット
uspto-grants-2008_06
特許番号
US07388023B2

関連ノート

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