Hydrogen Peroxide → Ammonium Bicarbonate

HRID 130905

反応式

HRID 130905 の反応式
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[OH:12])[CH:7]=O)[CH3:2].[C:13]([O-:16])([O-:15])=[O:14].[K+].[K+].F[C:20]1[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][CH:21]=1.[CH3:28][CH:29]([CH3:33])[CH2:30][CH2:31][NH2:32].[OH:34]O>CN(C=O)C>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH2:7][NH:32][CH2:31][CH2:30][CH:29]([CH3:33])[CH3:28])[CH:9]=[CH:10][C:11]=1[O:12][C:20]1[CH:27]=[CH:26][C:23]([C:24]([NH2:25])=[O:34])=[CH:22][CH:21]=1)[CH3:2].[C:13](=[O:14])([OH:16])[O-:15].[NH4+:25]

参加物

8

反応物 5

HCID 784Hydrogen PeroxideHCID 7894IsoamylamineHCID 8467EthylvanillinHCID 11430Potassium Carbonate2 回HCID 145174-Fluorobenzonitrile

生成物 2

HCID 14013Ammonium BicarbonateHCID 59729983HCID 59729983、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
130 °C

実験手順

Dissolve 3-ethoxy-4-hydroxy-benzaldehyde (2.57 g, 15.45 mmol) in DMF (20 mL), add K2CO3 (2.33 g, 16.86 mmol) and 4-fluorobenzonitrile (1.70 g, 14.05 mmol), heat the mixture at 130° C. overnight. Add water and extract the aqueous layer with EtOAc. Combine organic layers and dry over Na2SO4. Eliminate the solvent and purify by flash chromatography on silica gel (eluent: EtOAc/hexane 15/85) to get a mixture of two compounds (1.45 g). This mixture (240 mg) is submitted to the reductive amination conditions described for compound 1 (step 3) using 3-methyl-butylamine to obtain a mixture of two compounds which is subject to hydrolysis using hydrogen peroxide and potassium carbonate in the conditions described elsewhere in this document. This mixture is purified by flash chromatography (EtOAc and CH2Cl2/MeOH 10%) and then the title compound is isolated after HPLC (Column: XTerraMSC18 (5 um, 19×100 mm). Isocratic mode: 55/45 Ammonium bicarbonate-pH 9-/Acetonitrile. Flow: 10 mL/min).

後処理

  1. extractionAdd water and extract the aqueous layer with EtOAc
  2. dry with materialCombine organic layers and dry over Na2SO4
  3. custompurify by flash chromatography on silica gel (eluent: EtOAc/hexane 15/85)
  4. customto get
  5. customto obtain
  6. additiona mixture of two compounds which
  7. customis subject to hydrolysis
  8. customThis mixture is purified by flash chromatography (EtOAc and CH2Cl2/MeOH 10%)

出典と根拠

ORDレコード
ord-cc0e8454054e4ccdb4c60b683943b774
出典データセット
uspto-grants-2008_06
特許番号
US07381719B2

関連ノート

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