2,3-Dimethylbenzoic acid → Tert-butyl 4-(benzo[1,3]dioxol-5-yl)-2-(2,3-dimethylbenzamido)benzoate

HRID 1673443

反応式

HRID 1673443 の反応式
C(Cl)(=O)C(Cl)=O.[CH3:7][C:8]1[C:16]([CH3:17])=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=O.[NH2:18][C:19]1[CH:31]=[C:30]([C:32]2[CH:40]=[CH:39][C:35]3[O:36][CH2:37][O:38][C:34]=3[CH:33]=2)[CH:29]=[CH:28][C:20]=1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22].C(=O)([O-])O.[Na+]>C(N(CC)CC)C.C(Cl)Cl.CN(C)C=O>[O:36]1[C:35]2[CH:39]=[CH:40][C:32]([C:30]3[CH:29]=[CH:28][C:20]([C:21]([O:23][C:24]([CH3:26])([CH3:27])[CH3:25])=[O:22])=[C:19]([NH:18][C:10](=[O:12])[C:9]4[CH:13]=[CH:14][CH:15]=[C:16]([CH3:17])[C:8]=4[CH3:7])[CH:31]=3)=[CH:33][C:34]=2[O:38][CH2:37]1

参加物

8

反応物 4

HCID 117822,3-Dimethylbenzoic acidHCID 65578Oxalyl chlorideHCID 516892Sodium BicarbonateHCID 67342168Tert-butyl 2-amino-4-(benzo[1,3]dioxol-5-yl)benzoate

生成物 1

HCID 67342913Tert-butyl 4-(benzo[1,3]dioxol-5-yl)-2-(2,3-dimethylbenzamido)benzoate

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒2 回HCID 8471Triethylamine溶媒

実験手順

1.7 mL of methylene chloride, 1.0 μL N,N-dimethylformamide and 0.025 mL of oxalyl chloride were added to 41 mg of 2,3-dimethylbenzoic acid at room temperature sequentially and stirred ad the same temperature for 1 hour. The reaction mixture was added to a mixed solution of 50 mg of tert-butyl 2-amino-4-(benzo[1,3]dioxol-5-yl)benzoate, 2.8 mL of methylene chloride and 0.36 mL of triethylamine and stirred at room temperature for 1 hour. A saturated sodium hydrogen carbonate aqueous solution was added to the reaction mixture, and the organic layer was separated, and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [Flash Tube 2008 manufactured by Trikonex Company, eluent; hexane:ethyl acetate=4:1]to obtain tert-butyl 4-(benzo[1,3]dioxol-5-yl)-2-(2,3-dimethylbenzamido)benzoate.

後処理

  1. stirringstirred at room temperature for 1 hour
  2. customthe organic layer was separated
  3. customthe solvent was evaporated under reduced pressure
  4. customThe obtained residue was purified with silica gel column chromatography [Flash Tube 2008

出典と根拠

ORDレコード
ord-34f7e69ca54144a6b2fbb6e009767c56
出典データセット
uspto-grants-2011_08
特許番号
US07999132B2

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