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

HRID 29770노트

반응식

HRID 29770 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-54ecf76dce5245d5a20e5eab56e19121
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423012B2

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