Acetic Acid → 2-(6-Tert-butoxycarbonylaminopyridin-3-ylmethylene)-malonic acid diethyl ester

HRID 1789851Notes

Reaction equation

HRID 1789851 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:12]([O:16][C:17](=[O:27])[NH:18][C:19]1[CH:24]=[CH:23][C:22]([CH:25]=O)=[CH:21][N:20]=1)([CH3:15])([CH3:14])[CH3:13].N1CCCCC1.C(O)(=O)C>C(Cl)Cl.CN(C=O)C.CCCCCCC>[CH2:10]([O:9][C:1](=[O:8])[C:2](=[CH:25][C:22]1[CH:21]=[N:20][C:19]([NH:18][C:17]([O:16][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:27])=[CH:24][CH:23]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH3:11]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 7761Diethyl MalonateHCID 8082PiperidineHCID 22034247tert-butyl N-(5-formylpyridin-2-yl)carbamate

Product 1

HCID 543379912-(6-Tert-butoxycarbonylaminopyridin-3-ylmethylene)-malonic acid diethyl esterYield 40.3%

Reagents, catalysts & solvents 2

HCID 8900HeptaneSolventHCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

To a solution of diethyl malonate (710 μL, 4.7 mmol) and (5-formyl-pyridin-2-yl)-carbamic acid tert-butyl ester (1.04 g, 4.7 mmol) in methylene chloride/DMF (1:1, 5 mL) was added piperidine (46 μL, 0.47 mmol) and acetic acid (27 μL, 0.47 mmol). The reaction mixture was stirred for 72 h at room temperature and then for 16 h at 45° C. Heptane was added slowly to give 2-(6-tert-butoxycarbonylaminopyridin-3-ylmethylene)-malonic acid diethyl ester (0.69 g, 40%) as grey crystals.

Workup

  1. waitfor 16 h at 45° C

Sources & evidence

ORD record
ord-855ca57819ec4d568df1a98193a2fafc
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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