Cyclopropanecarboximidamide hydrochloride → HCID 178471100, compound

HRID 249648Notes

Reaction equation

HRID 249648 reaction equation
[CH2:1]([O:3][CH:4]([O:13][CH2:14][CH3:15])[C:5](=O)[CH2:6][C:7]([O:9]CC)=O)[CH3:2].Cl.[CH:17]1([C:20](=[NH:22])[NH2:21])[CH2:19][CH2:18]1.C[O-].[Na+]>CO>[CH:17]1([C:20]2[NH:22][C:5]([CH:4]([O:3][CH2:1][CH3:2])[O:13][CH2:14][CH3:15])=[CH:6][C:7](=[O:9])[N:21]=2)[CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 2781916Cyclopropanecarboximidamide hydrochlorideHCID 10942334Sodium MethoxideHCID 11138577Ethyl 4,4-diethoxy-3-oxobutanoate

Product 1

HCID 178471100HCID 178471100, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a mixture of ethyl 4,4-diethoxy-3-oxobutanoate (prepared according to the method of E. Graf, R. Troschutz, Synthesis, 1999, 7, 1216; 10.0 g, 46 mmol) and cyclopropane-carboximidamide monohydrochloride (Lancaster Synthesis, 5.0 g, 41 mmol) in methanol (100 mL) was added a methanol solution of sodium methoxide (5.4 M, 8.4 mL, 46 mmol). The reaction mixture was stirred overnight. The solvent was removed with a rotary evaporator. Dichloromethane was added and the mixture was filtered. The solvent from the filtrate was removed with a rotary evaporator. The residue was purified by medium pressure liquid chromatography (MPLC) (35→100% ethyl acetate in hexanes as eluant) to afford the title compound as a white solid (4.67 g).

Workup

  1. customprepared
  2. customTroschutz, Synthesis, 1999, 7, 1216
  3. customThe solvent was removed with a rotary evaporator
  4. additionDichloromethane was added
  5. filtrationthe mixture was filtered
  6. customThe solvent from the filtrate was removed with a rotary evaporator
  7. customThe residue was purified by medium pressure liquid chromatography (MPLC) (35→100% ethyl acetate in hexanes as eluant)

Sources & evidence

ORD record
ord-32039c26757042e6aec5cb0b0ab72d35
Source dataset
uspto-grants-2011_01
Patent number
US07863220B2

Reaction notes

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