Ethyl trifluoromethanesulphonate → (4R,5S)-[(S)-2-(2,4-Difluoro-benzyl)-butyryl]-4-methyl-5-phenyl-oxazolidin-2-one

HRID 349817

反応式

HRID 349817 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]([N:13]1[C@H:17]([CH3:18])[C@H:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[O:15][C:14]1=[O:25])=[O:12].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].O([CH2:44][CH3:45])S(C(F)(F)F)(=O)=O>C1COCC1>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C@H:10]([CH2:44][CH3:45])[C:11]([N:13]1[C@H:17]([CH3:18])[C@H:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[O:15][C:14]1=[O:25])=[O:12]

参加物

5

反応物 3

HCID 67924Ethyl trifluoromethanesulphonateHCID 2724254Sodium bis(trimethylsilyl)amideHCID 69267110(4R,5S)-3-[3-(2,4-Difluoro-phenyl)-propionyl]-4-methyl-5-phenyl-oxazolidin-2-one

生成物 1

HCID 69267273(4R,5S)-[(S)-2-(2,4-Difluoro-benzyl)-butyryl]-4-methyl-5-phenyl-oxazolidin-2-one収率 50.6%

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

A flask was charged with 54 g (156 mmol) of (4R,5S)-3-[3-(2,4-difluoro-phenyl)-propionyl]-4-methyl-5-phenyl-oxazolidin-2-one and 300 mL of dry THF, and the solution was cooled to −78° C. To this solution was added 172 mL (172 mmol) of 1 M NaHMDS in THF, and the mixture was stirred cold for 1 hour. Then 30.6 g (172 mmol) of ethyl triflate was added dropwise to the enolate solution, and the reaction mixture was warmed to 40° C. to −30° C. and stirred for 1.5 hours. The reaction mixture was quenched by the addition of aqueous brine. The THF was removed under reduced pressure and the residue was partitioned between EtOAc and water. The organics were collected, and EtOAc was removed under reduced pressure. The resulting crude oil was purified by column chromatography (3:1 hexanes/EtOAc eluent) to get 29.5 g of an impure oil that was used without further purification.

後処理

  1. temperaturethe reaction mixture was warmed to 40° C. to −30° C.
  2. stirringstirred for 1.5 hours
  3. customThe reaction mixture was quenched by the addition of aqueous brine
  4. customThe THF was removed under reduced pressure
  5. customthe residue was partitioned between EtOAc and water
  6. customThe organics were collected
  7. customEtOAc was removed under reduced pressure
  8. customThe resulting crude oil was purified by column chromatography (3:1 hexanes/EtOAc eluent)

出典と根拠

ORDレコード
ord-a1e81ac58b814f2586bfb6abf701331b
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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