Acetamidomalonic acid diethyl ester → HCID 23503295, compound

HRID 1835275Notes

Reaction equation

HRID 1835275 reaction equation
Cl[CH2:2][C:3]1[C:8]([CH2:9][Cl:10])=[N:7][CH:6]=[CH:5][N:4]=1.[CH2:11]([O:13][C:14](=[O:25])[CH:15]([NH:21][C:22](=[O:24])[CH3:23])[C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH3:12]>C(Cl)Cl>[C:22]([NH:21][C:15]([CH2:2][C:3]1[C:8]([CH2:9][Cl:10])=[N:7][CH:6]=[CH:5][N:4]=1)([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:14]([O:13][CH2:11][CH3:12])=[O:25])(=[O:24])[CH3:23]

Participants

4

Reactant 2

HCID 14041Acetamidomalonic acid diethyl esterHCID 132210262,3-Bis(chloromethyl)pyrazine

Product 1

HCID 23503295HCID 23503295, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,3-bis(chloromethyl)pyrazine (2.06 g, 11.64 mmol) in 60 mL DCM was added diethyl(N-acetylamino)malonate (2.66 g, 11.7 mmol)anhydrous potassium carbonate (4.83, 34.9 mmol) and 18-C-6 (154 mg, 5 mol %) and the reaction was stirred for 48 h. The reaction was filtered through a sintered glass funnel, concentrated, and flash chromatographed on SiO2 using a 50% to 75% EtOAc in hexane gradient. Obtained 3.06 g or 56% yield of the product. MS found: (M+H)+=359.

Workup

  1. filtrationThe reaction was filtered through a sintered glass funnel
  2. concentrationconcentrated
  3. customflash chromatographed on SiO2 using a 50% to 75% EtOAc in hexane gradient

Sources & evidence

ORD record
ord-d18f9b65815f4ec9a1774e8a4eeb5e9b
Source dataset
uspto-grants-2004_08
Patent number
US06770647B2

Reaction notes

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