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

HRID 1789852
Notes
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Reaction equation

HRID 1789852 reaction equation
[Li][CH3:2].[CH2:3]([O:5][C:6](=[O:28])[C:7](=[CH:13][C:14]1[CH:15]=[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][CH2:11][CH3:12])=[O:9])[CH3:4].[NH4+].[OH-]>C1COCC1.[Cu]I>[CH2:11]([O:10][C:8](=[O:9])[CH:7]([CH:13]([C:14]1[CH:15]=[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)[CH3:2])[C:6]([O:5][CH2:3][CH3:4])=[O:28])[CH3:12]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 543379912-(6-Tert-butoxycarbonylaminopyridin-3-ylmethylene)-malonic acid diethyl esterHCID 178418348HCID 178418348, compound

Product 1

HCID 542132152-[1-(6-Tert-butoxycarbonylamino-pyridin-3-yl)-ethyl]-malonic acid diethyl esterYield 82.6%

Reagents, catalysts & solvents 2

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Catalyst
HCID 8028TetrahydrofuranSolvent2×

Procedure

MeLi (6.5 mL, 10.4 mmol, 1.6 M in diethyl ether) was added dropwise to a slurry of CuI (0.9 g, 4.73 mmol) in THF (28 mL) at −78° C. under argon. The reaction mixture was stirred for 30 min. A solution of 2-(6-tert-butoxycarbonylamino-pyridin-3-ylmethylene)-malonic acid diethyl ester (0.84 g, 2.3 mmol) in THF (7 mL) was added dropwise and the reaction was stirred for 180 min at −78° C. Saturated aqueous NH4OH was added dropwise and the mixture was extracted with EtOAc. The organic phase was washed with saturated aqueous NH4OH and NaCl, dried and concentrated under reduced pressure. Flash chromatography (toluene/EtOAc, 3:1→1:6) gave 2-[1-(6-tert-butoxycarbonylamino-pyridin-3-yl)-ethyl]-malonic acid diethyl ester (0.723 g, 82.4%) as a white solid.

Workup

  1. stirringthe reaction was stirred for 180 min at −78° C
  2. extractionthe mixture was extracted with EtOAc
  3. washThe organic phase was washed with saturated aqueous NH4OH and NaCl
  4. customdried
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b2e368cb3ea14d72b8d97f1aee77e1cd
Source dataset
uspto-grants-2006_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07071175B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes