1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 2-[2-(3-Methyl-4-nitrophenyl)acetoxymethyl]-2-phenyl-malonic acid diethyl ester

HRID 494385Notes

Reaction equation

HRID 494385 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:11][C:12]([OH:14])=[O:13])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[CH2:15]([O:17][C:18](=[O:33])[C:19]([CH2:31]O)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH3:16].Cl.C(N=C=NCCCN(C)C)C>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH2:23]([O:22][C:20](=[O:21])[C:19]([CH2:31][O:13][C:12](=[O:14])[CH2:11][C:4]1[CH:5]=[CH:6][C:7]([N+:8]([O-:10])=[O:9])=[C:2]([CH3:1])[CH:3]=1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:18]([O:17][CH2:15][CH3:16])=[O:33])[CH3:24]

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 107503542-(3-Methyl-4-nitrophenyl)acetic acidHCID 22236963Diethyl 2-(hydroxymethyl)-2-phenylmalonate

Product 1

HCID 576832232-[2-(3-Methyl-4-nitrophenyl)acetoxymethyl]-2-phenyl-malonic acid diethyl esterYield 67.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

The (3-Methyl-4-nitrophenyl)acetic acid (0.143 g) obtained in Example 1-3b) was dissolved in methylene chloride (5 mL). To the solution were added 2-hydroxymethyl-2-phenylmalonic acid diethyl ester (0.195 g) obtained in Example 1-2a), 4-dimethylaminopyridine (0.090 g) and 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (0.141 g), and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated and the residue was purified by column chromatography on silica gel with ethyl acetate:hexane=1:4 to give the title compound (0.219 g) as a yellow oil.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by column chromatography on silica gel with ethyl acetate

Sources & evidence

ORD record
ord-5e04f4c6cef04b1e9474e82dfa5fa305
Source dataset
uspto-grants-2009_05
Patent number
US07538140B2

Reaction notes

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