Potassium Iodide → HCID 90281985、化合物

HRID 1497521ノート

反応式

HRID 1497521 の反応式
Cl[CH2:2][C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][CH:15]=1)[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].[NH2:16][C:17]1[CH:29]=[CH:28][C:20]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O.O>[C:24]([O:23][C:21]([C:20]1[CH:19]=[CH:18][C:17]([NH:16][CH2:2][C:3]2[CH:4]=[C:5]([CH:13]=[CH:14][CH:15]=2)[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[CH:29][CH:28]=1)=[O:22])([CH3:27])([CH3:25])[CH3:26]

参加物

7

反応物 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 233272Benzoic acid, 4-amino-, 1,1-dimethylethyl esterHCID 22456708tert-Butyl 3-(chloromethyl)benzoate

生成物 1

HCID 90281985HCID 90281985、化合物収率 79.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

To a solution of tert-butyl 3-(chloromethyl)benzoate (500 mg) in N,N-dimethylformamide (10.0 mL) were added tert-butyl 4-aminobenzoate (426 mg), potassium carbonate (610 mg), and potassium iodide (36.6 mg), followed by stirring at 60° C. overnight. To the reaction suspension was added water, followed by extraction with ethyl acetate. The organic layer was washed with water and a saturated aqueous sodium chloride solution, then dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain tert-butyl 3-({[4-(tert-butoxycarbonyl)phenyl]amino}methyl)benzoate (671 mg).

後処理

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materiala saturated aqueous sodium chloride solution, then dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

出典と根拠

ORDレコード
ord-bc7b3714def04d51a66758cecd8ab3b9
出典データセット
uspto-grants-2015_12
特許番号
US09199927B2

反応ノート

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