Potassium Hydroxide → 2-(2-Tert-butoxycarbonylamino-pyridin4-ylmethyl)-malonic acid monoethyl ester

HRID 1789797

Reaction equation

HRID 1789797 reaction equation
[OH-].[K+].[CH2:3]([O:5][C:6](=[O:28])[CH:7]([CH2:13][C:14]1[CH:19]=[CH:18][N:17]=[C:16]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH:15]=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:19]=[CH:18][N:17]=[C:16]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH:15]=1)[C:8]([OH:10])=[O:9])[CH3:4]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 545579702-(2-Tert-butoxycarbonylamino-pyridin4-ylmethyl)-malonic acid diethyl ester

Product 1

HCID 545486422-(2-Tert-butoxycarbonylamino-pyridin4-ylmethyl)-malonic acid monoethyl esterYield 81.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of KOH (0.19 g, 3.43 mmol) in ethanol (5 mL) was added to a solution of 2-(2-tert-butoxycarbonylamino-pyridin4-ylmethyl)-malonic acid diethyl ester (1.20 g, 3.27 mmol) in ethanol (5 mL) and methylene chloride (5 mL) at 0° C. The mixture was stirred for 18 h at room temperature. The mixture was concentrated under reduced pressure and water was added to the residue. The aqueous layer was washed with diethyl 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 evaporation in vacuo, the crude product was purified by flash chromatography (CH3OH/CH2Cl2, 1:20) to yield 2-(2-tert-butoxycarbonylamino-pyridin4-ylmethyl)-malonic acid monoethyl ester (0.90 g, 81%).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure and water
  2. additionwas added to the residue
  3. washThe aqueous layer was washed with diethyl ether
  4. extractionextracted with methylene chloride
  5. washThe organic layer was washed with water, brine
  6. customdried
  7. filtrationAfter filtration and evaporation in vacuo
  8. customthe crude product was purified by flash chromatography (CH3OH/CH2Cl2, 1:20)

Sources & evidence

ORD record
ord-d245cc3b73f8448fb111e6ba4a53d5dd
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Linked notes

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