Acetic Acid → 1-(4-Methoxybenzyl)indolin-5-yl 4-isopropylphenylcarbamate

HRID 2360137ノート

反応式

HRID 2360137 の反応式
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:22])[O:12][C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[NH:18][CH2:17][CH2:16]3)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[CH3:23][O:24][C:25]1[CH:32]=[CH:31][C:28]([CH:29]=O)=[CH:27][CH:26]=1.C(O)(=O)C.[Na].C([O-])(O)=O.[Na+]>ClCCl.C(OCC)C>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([NH:10][C:11](=[O:22])[O:12][C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[N:18]([CH2:29][C:28]2[CH:31]=[CH:32][C:25]([O:24][CH3:23])=[CH:26][CH:27]=2)[CH2:17][CH2:16]3)=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

参加物

8

反応物 5

HCID 176Acetic AcidHCID 312444-MethoxybenzaldehydeHCID 516892Sodium BicarbonateHCID 5360545SodiumHCID 86659865Indolin-5-yl 4-isopropylphenylcarbamate

生成物 1

HCID 866598661-(4-Methoxybenzyl)indolin-5-yl 4-isopropylphenylcarbamate収率 82%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of indolin-5-yl 4-isopropylphenylcarbamate (15.0 mg, 50.6 μmol) in 0.75 mL of dry dichloromethane was added 4-methoxybenzaldehyde (12.3 μL, 0.101 mmol) at room temperature. After the reaction mixture was stirred at the same temperature for 2 min, acetic acid (29 μL, 0.51 mmol) and sodium triacetoxyhydroborate (38 mg, 0.18 mmol) was added, successively. After the reaction mixture was stirred at the same temperature for 30 min, the reaction mixture was diluted with diethyl ether (2 mL). After the reaction mixture was neutralized by saturated NaHCO3 aqueous solution (1 mL), the organic layer was separated. The separated organic layer was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10 to 50/50) to obtain the title compound as a white solid (17.2 mg, 82%).

後処理

  1. stirringAfter the reaction mixture was stirred at the same temperature for 30 min
  2. customthe organic layer was separated
  3. concentrationThe separated organic layer was concentrated in vacuo
  4. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10 to 50/50)

出典と根拠

ORDレコード
ord-7be1648dfde04063b87cd26a82062301
出典データセット
uspto-grants-2014_04
特許番号
US08686024B2

反応ノート

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