Potassium Hydroxide → 2-[1-(6-Tert-butoxycarbonylamino-pyridin-3-yl)-ethyl]-malonic acid monoethyl ester

HRID 1789853Notes

Reaction equation

HRID 1789853 reaction equation
[OH-].[K+].[CH2:3]([O:5][C:6](=[O:29])[CH:7]([CH:13]([C:15]1[CH:16]=[N:17][C:18]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[CH:19][CH:20]=1)[CH3:14])[C:8]([O:10]CC)=[O:9])[CH3:4]>CCO.C(Cl)Cl>[CH2:3]([O:5][C:6](=[O:29])[CH:7]([CH:13]([C:15]1[CH:16]=[N:17][C:18]([NH:21][C:22]([O:24][C:25]([CH3:26])([CH3:28])[CH3:27])=[O:23])=[CH:19][CH:20]=1)[CH3:14])[C:8]([OH:10])=[O:9])[CH3:4]

Participants

5

Reactant 2

HCID 14797Potassium Hydroxide2×HCID 542132152-[1-(6-Tert-butoxycarbonylamino-pyridin-3-yl)-ethyl]-malonic acid diethyl ester

Product 1

HCID 696503142-[1-(6-Tert-butoxycarbonylamino-pyridin-3-yl)-ethyl]-malonic acid monoethyl esterYield 65.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of KOH (113.6 mg, 2.04 mmol) in EtOH (2 mL) was added dropwise to a solution of 2-[1-(6-tert-butoxycarbonylamino-pyridin-3-yl)-ethyl]-malonic acid diethyl ester (0.7 g, 1.84 mmol) in methylene chloride (4 mL) and EtOH (10 mL) at 0° C. under argon and the reaction mixture was stirred over night. 1M KOH (100 mL) was added and the mixture was washed with methylene chloride. The aqueous phase was acidified to pH 2 using 2 M HCl and extracted with EtOAc. The organic phase was dried and concentrated under reduced pressure to give the crude 2-[1-(6-tert-butoxycarbonylamino-pyridin-3-yl)-ethyl]-malonic acid monoethyl ester (423 mg, 65%).

Workup

  1. washthe mixture was washed with methylene chloride
  2. extractionextracted with EtOAc
  3. customThe organic phase was dried
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cd61fcaf6d09420faf778f4a0e3fa1f3
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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