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

HRID 1789917Notes

Reaction equation

HRID 1789917 reaction equation
[OH-].[K+].[CH2:3]([O:5][C:6](=[O:35])[CH:7]([CH:13]([C:21]1[CH:22]=[N:23][C:24]([NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[CH:25][CH:26]=1)[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:8]([O:10]CC)=[O:9])[CH3:4]>C(O)C.C(Cl)Cl>[CH2:3]([O:5][C:6](=[O:35])[CH:7]([CH:13]([C:21]1[CH:22]=[N:23][C:24]([NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[CH:25][CH:26]=1)[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:8]([OH:10])=[O:9])[CH3:4]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 540328992-[1-(6-Tert-butoxycarbonylamino-pyridin-3-yl)-2-phenyl-ethyl]-malonic acid diethyl ester

Product 1

HCID 539757352-[1-(6-Tert-butoxycarbonylamino-pyridin-3-yl)-2-phenyl-ethyl]-malonic acid monoethyl esterYield 90%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of KOH (0.067 g, 1.03 mmol) in ethanol (3 mL) was added to a solution of 2-[1-(6-tert-butoxycarbonylamino-pyridin-3-yl)-2-phenyl-ethyl]-malonic acid diethyl ester (0.44g, 0.96 mmol) in ethanol (3 mL) and methylene chloride (2 mL) at 0° C. The mixture was stirred for 48 h at room temperature. The mixture was concentrated under reduced pressure and ethyl acetate and 0.5 M HCl were added to the residue. The organic layer was washed with brine and dried. Filtration and evaporation in vacuo gave 2-[1-(6-tert-butoxycarbonylamino-pyridin-3-yl)-2-phenyl-ethyl]-malonic acid monoethyl ester (0.37, 90%).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure and ethyl acetate and 0.5 M HCl
  2. additionwere added to the residue
  3. washThe organic layer was washed with brine
  4. customdried
  5. filtrationFiltration and evaporation in vacuo

Sources & evidence

ORD record
ord-f601510239bb4196bfecd8efb5551d09
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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