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

HRID 1789912Notes

Reaction equation

HRID 1789912 reaction equation
[OH-].[K+].[CH2:3]([O:5][C:6](=[O:34])[CH:7]([CH:13]([C:20]1[CH:21]=[N:22][C:23]([NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[CH:24][CH:25]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][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:34])[CH:7]([CH:13]([C:20]1[CH:21]=[N:22][C:23]([NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[CH:24][CH:25]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:8]([OH:10])=[O:9])[CH3:4]

Participants

5

Reactant 2

HCID 14797Potassium Hydroxide2×HCID 544346512-[(6-Tert-butoxycarbonylamino-pyridin-3-yl)-phenyl-methyl]-malonic acid diethyl ester

Product 1

HCID 543127722-[(6-Tert-butoxycarbonylamino-pyridin-3-yl)-phenyl-methyl]-malonic acid monoethyl esterYield 99.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of KOH (0.266 g, 4.11 mmol) in ethanol (14 mL) was added to a solution of 2-[(6-tert-butoxycarbonylamino-pyridin-3-yl)-phenyl-methyl]-malonic acid diethyl ester (1.82 g, 4.11 mmol) in ethanol (12 mL) and methylene chloride (13 mL) at 0° C. The mixture was stirred overnight at room temperature. More KOH (80 mg dissolved in 3 mL ethanol) was added at 0° C. The reaction mixture was stirred for additional 18 h. 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. After filtration and evaporation in vacuo, the residue was suspended in hexane. Filtration of the crystals gave 2-[(6-tert-butoxycarbonylamino-pyridin-3-yl)-phenyl-methyl]-malonic acid monoethyl ester (1.7 g, 98%).

Workup

  1. stirringThe reaction mixture was stirred for additional 18 h
  2. concentrationThe mixture was concentrated under reduced pressure and ethyl acetate, and 0.5 M HCl
  3. additionwere added to the residue
  4. washThe organic layer was washed with brine
  5. customdried
  6. filtrationAfter filtration and evaporation in vacuo
  7. filtrationFiltration of the crystals

Sources & evidence

ORD record
ord-96bd72ab02c549c9994fa9edd37dec7e
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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