Cesium carbonate → 3-Neopentyl-7-(((2-nitro-5-(trifluoromethyl)phenyl)amino)methyl)-1-oxa-3-azaspiro[4.5]decan-2-one

HRID 1423844

反応式

[N+:1]([C:4]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].Br[CH2:16][CH:17]1[CH2:32][CH2:31][CH2:30][C:19]2([O:23][C:22](=[O:24])[N:21]([CH2:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:20]2)[CH2:18]1.C(=O)([O-])[O-].[Cs+].[Cs+].[Cl-].[NH4+]>CN(C=O)C>[CH2:25]([N:21]1[CH2:20][C:19]2([CH2:30][CH2:31][CH2:32][CH:17]([CH2:16][NH:6][C:5]3[CH:7]=[C:8]([C:11]([F:12])([F:13])[F:14])[CH:9]=[CH:10][C:4]=3[N+:1]([O-:3])=[O:2])[CH2:18]2)[O:23][C:22]1=[O:24])[C:26]([CH3:29])([CH3:28])[CH3:27]

参加物

反応条件

温度: 60 °C

実験手順

A solution containing 2-nitro-5-(trifluoromethyl)aniline (0.777 g, 3.77 mmol) and 7-(bromomethyl)-3-neopentyl-1-oxa-3-azaspiro[4.5]decan-2-one (1.00 g, 3.14 mmol) in DMF (15 mL) was treated with cesium carbonate (3.07 g, 9.43 mmol) and stirred at 60° C. overnight. The cooled reaction mixture was diluted with saturated, aqueous ammonium chloride solution, and the product was extracted into DCM. The organics were washed with brine, dried over Na2SO4, and concentrated. The residue was purified on a 120 g silica gel column (10-60 EtOAc/hexanes; 65 mL/min elution; 254 nm detection) to afford the title compound (0.260 g, 19 yield). MS (m/z) 444.2 (M+H+).

後処理

customThe cooled reaction mixture
extractionthe product was extracted into DCM
washThe organics were washed with brine
dry with materialdried over Na2SO4
concentrationconcentrated
customThe residue was purified on a 120 g silica gel column (10-60 EtOAc/hexanes; 65 mL/min elution; 254 nm detection)

出典と根拠

ORDレコード: ord-b430131e6fab47568898c5403af08fa0
出典データセット: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US08927585B2

反応式

参加物

反応物 4

生成物 1

試薬・触媒・溶媒 1

反応条件

実験手順

後処理

出典と根拠

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