Quinone → HCID 700990, compound

HRID 250249Notes

Reaction equation

HRID 250249 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[CH:5]=[C:6]([NH:8][CH:9]1[CH2:11][CH2:10]1)[CH3:7])[CH3:2].[C:13]1(=O)[CH:18]=[CH:17][C:16](=[O:19])[CH:15]=[CH:14]1>C(O)(=O)C>[CH2:1]([O:3][C:4]([C:5]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([OH:19])[CH:17]=2)[N:8]([CH:9]2[CH2:11][CH2:10]2)[C:6]=1[CH3:7])=[O:12])[CH3:2]

Participants

4

Reactant 2

HCID 4650QuinoneHCID 67271584Ethyl 3-(cyclopropylamino)but-2-enoate

Product 1

HCID 700990HCID 700990, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Neat 3-cyclopropylamino-but-2-enoic acid ethyl ester (5.63 g, 33.2 mmol) is added to a mixture of p-benzoquinone (7.19 g, 66.5 mmol) and acetic acid (120 mL). The mixture is stirred at room temperature for 5 h and a dark solid is precipitated. The solid is washed with acetic acid and water, dried, adsorbed onto silica gel, and purified via flash chromatography eluting with dichloromethane. The product is triturated in dichloromethane-hexane to afford the title compound (440 mg, 21%). ES/MS m/e 260.0 (M+1)

Workup

  1. customa dark solid is precipitated
  2. washThe solid is washed with acetic acid and water
  3. customdried
  4. custompurified via flash chromatography
  5. washeluting with dichloromethane
  6. customThe product is triturated in dichloromethane-hexane

Sources & evidence

ORD record
ord-73c9913a9cf84f8aaa51b418b798c471
Source dataset
uspto-grants-2011_01
Patent number
US07863302B2

Reaction notes

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