Potassium Hydroxide → HCID 54417312, compound

HRID 1789887Notes

Reaction equation

HRID 1789887 reaction equation
[OH-].[K+].[CH2:3]([O:5][C:6](=[O:30])[CH:7]([CH2:13][C:14]1[CH:15]=[N:16][C:17]([NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[C:18]([CH:20]=[CH2:21])[CH:19]=1)[C:8]([O:10]CC)=[O:9])[CH3:4]>C(O)C.ClCCl>[CH2:3]([O:5][C:6](=[O:30])[CH:7]([CH2:13][C:14]1[CH:15]=[N:16][C:17]([NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[C:18]([CH:20]=[CH2:21])[CH:19]=1)[C:8]([OH:10])=[O:9])[CH3:4]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 54344379HCID 54344379, compound

Product 1

HCID 54417312HCID 54417312, compoundYield 76.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of KOH (0.71 g, 12.6 mmol, 85%) in ethanol (10 ml) was added to a solution of 2-(6-tert-butoxycarbonylamino-5-vinyl-pyridin-3-ylmethyl)-malonic acid diethyl ester (4.30 g, 11.0 mmol) in ethanol (25 ml) and dichloromethane (10 ml) at 0° C. The mixture was stirred for 6 h at room temperature. The solvent was evaporated in vacuo and the residue dissolved in water. The aqueous layer was washed with ether, acidified to pH 4 by 1 M HCl and extracted with dichloromethane. The organic layer was washed with water and brine and dried. Filtration and concentration under reduced pressure followed by flash chromatography (10% MeOH in CH2Cl2) gave 2-(6tert-butoxycarbonylamino5-vinyl-pyridin-3-ylmethyl)-malonic acid monoethyl ester (3.05 g, 76%).

Workup

  1. customThe solvent was evaporated in vacuo
  2. dissolutionthe residue dissolved in water
  3. washThe aqueous layer was washed with ether
  4. extractionextracted with dichloromethane
  5. washThe organic layer was washed with water and brine
  6. customdried
  7. filtrationFiltration and concentration under reduced pressure

Sources & evidence

ORD record
ord-daf3c758d7854f07aad3e69c2d3882de
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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