Cesium carbonate → Tert-Butyl Cyclopentyl{4-[(5-oxo-2-phenyl-5,6-dihydro-4H-1,3,4-oxadiazin-4-yl)methyl]phenyl}-acetate

HRID 877157ノート

反応式

HRID 877157 の反応式
[C:1]([O:5][C:6](=[O:21])[CH:7]([C:13]1[CH:18]=[CH:17][C:16]([CH2:19]Br)=[CH:15][CH:14]=1)[CH:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[C:22]1([C:28]2[O:29][CH2:30][C:31](=[O:34])[NH:32][N:33]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(=O)(O)[O-].[Na+]>CN(C=O)C>[CH:8]1([CH:7]([C:13]2[CH:18]=[CH:17][C:16]([CH2:19][N:32]3[C:31](=[O:34])[CH2:30][O:29][C:28]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[N:33]3)=[CH:15][CH:14]=2)[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:21])[CH2:12][CH2:11][CH2:10][CH2:9]1

参加物

6

反応物 4

HCID 10796Cesium carbonateHCID 516892Sodium BicarbonateHCID 142034742-phenyl-5,6-dihydro-4H-1,3,4-oxadiazin-5-oneHCID 15225592tert-Butyl 2-(4-(bromomethyl)phenyl)-2-cyclopentylacetate

生成物 1

HCID 58074542Tert-Butyl Cyclopentyl{4-[(5-oxo-2-phenyl-5,6-dihydro-4H-1,3,4-oxadiazin-4-yl)methyl]phenyl}-acetate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

8.16 g (23.1 mmol) of tert-butyl[4-(bromomethyl)phenyl](cyclopentyl)acetate, 3.7 g (21 mmol) of 2-phenyl-4H-1,3,4-oxadiazin-5(6H)-one and 7.53 g (23.1 mmol) of cesium carbonate were stirred in 147 ml of DMF at room temperature for 12 h. The reaction solution was then stirred with saturated aqueous sodium bicarbonate solution and extracted twice with ethyl acetate. The combined organic phases were dried over magnesium sulfate and concentrated to dryness under reduced pressure. The crude product obtained was purified chromatographically on silica gel (mobile phase cyclohexane/ethyl acetate 5:1). This gave 6.51 g (14.5 mmol, 69% of theory) of the title compound.

後処理

  1. extractionextracted twice with ethyl acetate
  2. dry with materialThe combined organic phases were dried over magnesium sulfate
  3. concentrationconcentrated to dryness under reduced pressure

出典と根拠

ORDレコード
ord-4191b7084fca4ac8a5c6b004c528665a
出典データセット
uspto-grants-2015_03
特許番号
US08987256B2

反応ノート

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