Ethanol → 2-(6-Tert-butoxycarbonylamino-pyridin-3-ylmethyl)-3-butyl-2-ethoxycarbonyl-succinic acid diethyl ester

HRID 29770ノート

反応式

HRID 29770 の反応式
[CH2:1]([O:3][C:4](=[O:21])[CH:5]([CH2:17][CH2:18][CH2:19][CH3:20])[CH:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH3:2].[H-].[Na+].[C:24]([O:28][C:29](=[O:39])[NH:30][C:31]1[CH:36]=[CH:35][C:34]([CH2:37]Br)=[CH:33][N:32]=1)([CH3:27])([CH3:26])[CH3:25].C(O)C>CN(C=O)C.O>[CH2:10]([O:9][C:7](=[O:8])[C:6]([CH2:37][C:34]1[CH:33]=[N:32][C:31]([NH:30][C:29]([O:28][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:39])=[CH:36][CH:35]=1)([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:5]([CH2:17][CH2:18][CH2:19][CH3:20])[C:4]([O:3][CH2:1][CH3:2])=[O:21])[CH3:11]

参加物

7

反応物 4

HCID 702EthanolHCID 24758Sodium hydrideHCID 134450202-Butyl-3-ethoxycarbonyl-succinic acid diethyl esterHCID 23030321tert-Butyl (5-(bromomethyl)pyridin-2-yl)carbamate

生成物 1

HCID 542435252-(6-Tert-butoxycarbonylamino-pyridin-3-ylmethyl)-3-butyl-2-ethoxycarbonyl-succinic acid diethyl ester収率 78.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

A solution of 2-butyl-3-ethoxycarbonyl-succinic acid diethyl ester (1 g, 3 mmol) and NaH (119 mg, 5 mmol) in DMF (20 ml) was stirred for 60 minutes at 0° C. under argon. (5-Bromomethyl-pyridin-2-yl)-carbamic acid tert-butyl ester (1.425 g, 5 mmol) was added and the mixture was stirred at room temperature for one week. Ethanol (1 ml) was added and the reaction was poured into H2O and extracted with ethyl acetate. The organic layer was washed with water and concentrated under reduced pressure. The product was purified by column chromatography (heptane/ethyl acetate, 4:1 to 1:1) to give 2-(6-tert-butoxycarbonylamino-pyridin-3-ylmethyl)-3-butyl-2-ethoxycarbonyl-succinic acid diethyl ester (1.2 g, 71.3%).

後処理

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. concentrationconcentrated under reduced pressure
  4. customThe product was purified by column chromatography (heptane/ethyl acetate, 4:1 to 1:1)

出典と根拠

ORDレコード
ord-54ecf76dce5245d5a20e5eab56e19121
出典データセット
uspto-grants-2008_09
特許番号
US07423012B2

反応ノート

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