Triethylamine → 3-(2-Methyl-pent-2-enoyl)-4-phenyl-oxazolidin-2-one

HRID 349823

反応式

HRID 349823 の反応式
F[C:2]1[CH:7]=[C:6](F)[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10]C(O)=O.[CH3:14][C:15]([CH3:20])(C)[C:16](Cl)=[O:17].[Li+].[Cl-].C[C@H]1[C@@H](C2C=CC=CC=2)[O:27][C:26](=[O:35])[NH:25]1.[CH2:36](N(CC)CC)[CH3:37]>C1COCC1>[CH3:14][C:15](=[CH:20][CH2:36][CH3:37])[C:16]([N:25]1[CH:9]([C:3]2[CH:2]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH2:10][O:35][C:26]1=[O:27])=[O:17]

参加物

7

反応物 5

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 433294Lithium ChlorideHCID 8531614-Methyl-5-phenyl-2-oxazolidinone, (4S,5R)-HCID 49863953-(2,4-difluorophenyl)propanoic Acid

生成物 1

HCID 690482483-(2-Methyl-pent-2-enoyl)-4-phenyl-oxazolidin-2-one収率 99%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran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 were 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 were 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-b24b07d8b7dc45fb9b56dd08ab118735
出典データセット
uspto-grants-2007_02
特許番号
US07179934B2

関連ノート

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