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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
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HRID 877157 반응식
[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
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참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4191b7084fca4ac8a5c6b004c528665a
출처 데이터셋
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08987256B2

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