Ethyl Acetate → HCID 54453537, compound

HRID 1789861Notes

Reaction equation

HRID 1789861 reaction equation
[OH-].[K+].[CH2:3]([O:5][C:6](=[O:29])[CH:7]([CH2:13][C:14]1[C:15]([CH3:28])=[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].CCOC(C)=O>CCO.CCO.C(Cl)Cl>[CH2:3]([O:5][C:6](=[O:29])[CH:7]([CH2:13][C:14]1[C:15]([CH3:28])=[N:16][C:17]([NH:20][C:21]([O:23][C:24]([CH3:26])([CH3:25])[CH3:27])=[O:22])=[CH:18][CH:19]=1)[C:8]([OH:10])=[O:9])[CH3:4]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 14797Potassium HydroxideHCID 696502982-(6-Tert-butoxycarbonylamino-2-methyl-pyridin-3-ylmethyl)-malonic acid diethyl ester

Product 1

HCID 54453537HCID 54453537, compoundYield 84.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 21584144Dichloromethane ethanolSolvent

Procedure

A solution of KOH (300 mg, 5.35 mmol) in EtOH (4 mL) was added to a solution of 2-(6-tert-butoxycarbonylamino-2-methyl-pyridin-3-ylmethyl)-malonic acid diethyl ester (1.85 g, 4.86 mmol) in EtOH/methylene chloride (2:1, 21 mL) at 0° C. The mixture was stirred for 40 h at room temperature and EtOAc was added. The mixture was washed with 0.5 M HCl and brine, dried and concentrated under reduced pressure to give crude 2-(6-tert-butoxycarbonylamino-2-methyl-pyridin-3-ylmethyl)-malonic acid monoethyl ester (1.45 g).

Workup

  1. washThe mixture was washed with 0.5 M HCl and brine
  2. customdried
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-21fad67156264e4480b30ec1c771b74e
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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