Cesium carbonate → methyl 4-((4-acetoxy-N-(2-methoxybenzyl)phenylsulfonamido)methyl)benzoate

HRID 548076ノート

反応式

HRID 548076 の反応式
[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([S:11](=[O:23])(=[O:22])[NH:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH3:21])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:31][C:32]1[CH:41]=[CH:40][C:35]([C:36]([O:38][CH3:39])=[O:37])=[CH:34][CH:33]=1>CC(C)=O>[C:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]([S:11]([N:12]([CH2:31][C:32]2[CH:41]=[CH:40][C:35]([C:36]([O:38][CH3:39])=[O:37])=[CH:34][CH:33]=2)[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH3:21])(=[O:23])=[O:22])=[CH:9][CH:10]=1)(=[O:3])[CH3:2]

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 256687Methyl 4-(bromomethyl)benzoateHCID 574223444-(N-(2-methoxybenzyl)sulfamoyl)phenyl acetate

生成物 1

HCID 66974740methyl 4-((4-acetoxy-N-(2-methoxybenzyl)phenylsulfonamido)methyl)benzoate

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

4-(N-(2-methoxybenzyl)sulfamoyl)phenyl acetate (example 5-42a) (50 mg, 0.15 mmol) was dissolved in acetone (1.0 mL) followed by the addition of cesium carbonate (97 mg, 0.30 mmol) and methyl 4-(bromomethyl)benzoate (38 mg, 0.17 mmol). The mixture was stirred at room temperature overnight and then the inorganic salts were filtered off. Acetone was removed in vacuo and the residue was re-dissolved in ethyl acetate and washed with water followed by brine. The organic layer was dried over magnesium sulfate and concentrated. The crude product was purified by column chromatography with ethyl acetate/hexanes as the eluent to afford methyl 4-((4-acetoxy-N-(2-methoxybenzyl)phenylsulfonamido)methyl)benzoate.

後処理

  1. filtrationthe inorganic salts were filtered off
  2. customAcetone was removed in vacuo
  3. dissolutionthe residue was re-dissolved in ethyl acetate
  4. washwashed with water
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe crude product was purified by column chromatography with ethyl acetate/hexanes as the eluent

出典と根拠

ORDレコード
ord-c3089ff3f82f461a8f841754f9a3115f
出典データセット
uspto-grants-2011_05
特許番号
US07939671B2

反応ノート

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