Potassium Carbonate → Diisopropyl(((2-((2-methoxyphenyl)carbamoyl)-3-((4-nitro-phenyl)thio)phenyl)amino)methyl)phosphonate

HRID 1476710

反応式

HRID 1476710 の反応式
[NH2:1][C:2]1[CH:18]=[CH:17][CH:16]=[C:15]([S:19][C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=2)[C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][CH3:14])=[O:5].C(=O)([O-])[O-].[K+].[K+].[CH:35]([O:38][P:39]([CH2:45]Br)(=[O:44])[O:40][CH:41]([CH3:43])[CH3:42])([CH3:37])[CH3:36]>CC#N>[CH:41]([O:40][P:39]([CH2:45][NH:1][C:2]1[CH:18]=[CH:17][CH:16]=[C:15]([S:19][C:20]2[CH:21]=[CH:22][C:23]([N+:26]([O-:28])=[O:27])=[CH:24][CH:25]=2)[C:3]=1[C:4](=[O:5])[NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][CH3:14])(=[O:44])[O:38][CH:35]([CH3:37])[CH3:36])([CH3:43])[CH3:42]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 4366885Diisopropyl bromomethylphosphonateHCID 718115872-amino-N-(2-methoxyphenyl)-6-(4-nitrophenyl-thio)benzamide

生成物 1

HCID 71811718Diisopropyl(((2-((2-methoxyphenyl)carbamoyl)-3-((4-nitro-phenyl)thio)phenyl)amino)methyl)phosphonate収率 41%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
60 °C

実験手順

Compound 25 (1.0 equiv.) was dissolved in MeCN (40 mL) and treated with anhydrous potassium carbonate (2.0 equiv.) at room temperature. To this mixture diisopropyl(bromomethyl)phosphonate (1.2 equiv.) was added via a micro syringe. After being stirred for 4 Hours at 60° C., the reaction mixture was concentrated under reduced pressure. The crude residue was diluted by ethyl acetate (50 mL), and washed with water (2×10 mL). Then it was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (1:4 v/v ethyl acetate/petroleum ether) to provide a yellow solid (235.2 mg, 41% yield).

後処理

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. additionThe crude residue was diluted by ethyl acetate (50 mL)
  3. washwashed with water (2×10 mL)
  4. dry with materialThen it was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (1:4 v/v ethyl acetate/petroleum ether)

出典と根拠

ORDレコード
ord-88db3d8f35ff41cca758454c7100483a
出典データセット
uspto-grants-2016_08
特許番号
US09402819B2

関連ノート

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