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Potassium Hydroxide → 2-(6-Tert-butoxycarbonylamino-pyridin-3-ylmethyl)-malonic acid monoethyl ester

HRID 1789806
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HRID 1789806 반응식
[OH-].[K+].[CH2:3]([O:5][C:6](=[O:28])[CH:7]([CH2:13][C:14]1[CH:15]=[N:16][C:17]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[CH:18][CH:19]=1)[C:8]([O:10]CC)=[O:9])[CH3:4]>C(O)C.C(Cl)Cl>[CH2:3]([O:5][C:6](=[O:28])[CH:7]([CH2:13][C:14]1[CH:15]=[N:16][C:17]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[CH:18][CH:19]=1)[C:8]([OH:10])=[O:9])[CH3:4]
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참가 물질

5

반응물 2

HCID 14797Potassium HydroxideHCID 544806432-(6-Tert-butoxycarbonylamino-pyridin-3-ylmethyl)-malonic acid diethyl ester

생성물 1

HCID 537177962-(6-Tert-butoxycarbonylamino-pyridin-3-ylmethyl)-malonic acid monoethyl ester수율 50%

시약·촉매·용매 2

HCID 702Ethanol용매2회HCID 6344Dichloromethane용매

실험 절차

A solution of KOH (0.37 g, 6.54 mmol) in ethanol (5 mL) was added to a solution of 2-(6-tert-butoxycarbonylamino-pyridin-3-ylmethyl)-malonic acid diethyl ester (2.18 g, 5.95 mmol) in ethanol (25 mL) and methylene chloride (10 mL) at 0° C. The mixture was stirred for 18 h at room temperature. The mixture was concentrated under reduced pressure and the residue dissolved in water. The aqueous layer was washed with ether, acidified to pH 4 by 1M HCl and extracted with methylene chloride. The organic layer was washed with water, brine and dried. After filtration and concentration under reduced pressure, the crude product was purified by flash chromatography (methanol/CH2Cl2, 1:20) to yield 2-(6-tert-butoxycarbonylamino-pyridin-3-ylmethyl)-malonic acid monoethyl ester (1.00 g, 50%).

후처리

  1. concentrationThe mixture was concentrated under reduced pressure
  2. dissolutionthe residue dissolved in water
  3. washThe aqueous layer was washed with ether
  4. extractionextracted with methylene chloride
  5. washThe organic layer was washed with water, brine
  6. customdried
  7. filtrationAfter filtration and concentration under reduced pressure
  8. customthe crude product was purified by flash chromatography (methanol/CH2Cl2, 1:20)

출처 및 근거

ORD 기록
ord-dcc7ced14d924601a79f1709878a8ac1
출처 데이터셋
uspto-grants-2006_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07071175B1

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