Sodium → 3-Amino-4-cyclopropyl-but-2-enoic acid ethyl ester

HRID 890487Notes

Reaction equation

HRID 890487 reaction equation
[NH2:1][C:2](=[C:7]1C(=O)O[C:10](C)([CH3:14])[O:9][C:8]1=[O:16])[CH2:3][CH:4]1[CH2:6][CH2:5]1.[Na].[Cl-].[Na+].O>C(O)C.ClCCl>[CH2:10]([O:9][C:8](=[O:16])[CH:7]=[C:2]([NH2:1])[CH2:3][CH:4]1[CH2:5][CH2:6]1)[CH3:14]

Participants

6

Reactant 3

HCID 5360545SodiumHCID 219356625-(1-Amino-2-cyclopropyl-ethylidene)-2,2-dimethyl-[1,3]dioxane-4,6-dioneHCID 57417360Sodium chloride; water

Product 1

HCID 670720963-Amino-4-cyclopropyl-but-2-enoic acid ethyl esterYield 77%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

5-(1-Amino-2-cyclopropyl-ethylidene)-2,2-dimethyl-[1,3]dioxane-4,6-dione (397 mg, 2 mmol) was added to a solution of sodium (45 mg, 2 mmol) in ethanol (3 ml). The reaction mixture was heated under reflux for 14 h, diluted with dichloromethane and poured onto ice water/brine 1/1. The organic layer was dried over sodium sulfate and the solvent removed under reduced pressure to give 231 mg (1.4 mmol, 77%) of the title compound as orange oil.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 14 h
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-a8b1e454f34343928467d1fa77b8abc0
Source dataset
uspto-grants-2006_02
Patent number
US06995263B2

Reaction notes

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