Bromoacetonitrile → (S)-3-(4-bromo-2-methoxy-phenyl)-4-((S)-4-isopropyl-2-oxo-oxazolidin-3-yl)-4-oxo-butyronitrile

HRID 503920ノート

反応式

HRID 503920 の反応式
[CH:1]([N-:4]C(C)C)(C)[CH3:2].[Li+].[Br:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17]([N:19]2[C@@H:23]([CH:24]([CH3:26])[CH3:25])[CH2:22][O:21][C:20]2=[O:27])=[O:18])=[C:12]([O:28][CH3:29])[CH:11]=1.BrCC#N.[NH4+].[Cl-]>C1COCC1>[Br:9][C:10]1[CH:15]=[CH:14][C:13]([C@@H:16]([C:17]([N:19]2[C@@H:23]([CH:24]([CH3:26])[CH3:25])[CH2:22][O:21][C:20]2=[O:27])=[O:18])[CH2:2][C:1]#[N:4])=[C:12]([O:28][CH3:29])[CH:11]=1

参加物

6

反応物 4

HCID 11534BromoacetonitrileHCID 25517Ammonium ChlorideHCID 2724682Lithium diisopropylamideHCID 66877012(S)-3-[2-(4-bromo-2-methoxy-phenyl)-acetyl]-4-isopropyl-oxazolidin-2-one

生成物 1

HCID 66877211(S)-3-(4-bromo-2-methoxy-phenyl)-4-((S)-4-isopropyl-2-oxo-oxazolidin-3-yl)-4-oxo-butyronitrile収率 60.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Lithium diisopropylamide (2.0 M in heptane/THF/ethylbenzene, 1.58 mL, 3.16 mmol) was added to a solution of (S)-3-[2-(4-bromo-2-methoxy-phenyl)-acetyl]-4-isopropyl-oxazolidin-2-one (1.126 g, 3.16 mmol) in THF (11 mL) under argon atmosphere at −78° C. The mixture was stirred for 15 minutes and bromoacetonitrile (0.23 mL, 3.32 mmol) was added at −78° C. The mixture was stirred for 3 hours at 0° C., and then a saturated solution of NH4Cl was added. The mixture was extracted with EtOAc, and the combined organic extracts were washed with brine, dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified via flash chromatography (hexane/EtOAc, 85/15) to give 755 mg (60% yield) of (S)-3-(4-bromo-2-methoxy-phenyl)-4-((S)-4-isopropyl-2-oxo-oxazolidin-3-yl)-4-oxo-butyronitrile as a white solid.

後処理

  1. stirringThe mixture was stirred for 3 hours at 0° C.
  2. extractionThe mixture was extracted with EtOAc
  3. washthe combined organic extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was purified via flash chromatography (hexane/EtOAc, 85/15)

出典と根拠

ORDレコード
ord-f802fb5a807045999ad86eadd2621f34
出典データセット
uspto-grants-2010_08
特許番号
US07776910B2

反応ノート

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