Hydrochloric Acid → N-[[1-[[(E)-3-(2-furanyl)-1-oxo-2-Propenyl]amino]cyclohexyl]carbonyl]-L-methionine

HRID 1627498Notes

Reaction equation

HRID 1627498 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1/[CH:6]=[CH:7]/[C:8]1C(=O)[C:11](=[O:14])[C:10]2([CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[N:9]=1.[NH2:20][C@H:21]([C:26]([OH:28])=[O:27])[CH2:22][CH2:23][S:24][CH3:25].C(OCC)(=[O:31])C.Cl>CN1CCOCC1.O>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1/[CH:6]=[CH:7]/[C:8]([NH:9][C:10]1([C:11]([NH:20][C@H:21]([C:26]([OH:28])=[O:27])[CH2:22][CH2:23][S:24][CH3:25])=[O:14])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1)=[O:31]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6137L-MethionineHCID 8857Ethyl AcetateHCID 67180194HCID 67180194, compound

Product 1

HCID 24737876N-[[1-[[(E)-3-(2-furanyl)-1-oxo-2-Propenyl]amino]cyclohexyl]carbonyl]-L-methionineYield 9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 79724-MethylmorpholineSolvent

Procedure

A solution of 491 mg (2 mmol) of 2-[(E)-2-(2-furanyl)ethenyl]-3-oxo-1-azaspiro[4.5]dec-1-en-4-one and 597 mg (4 mmol) of L-methionine in 20 ml of N-methylmorpholine was heated under reflux for 15 hours. After ethyl acetate and water were added to the reaction solution, it was acidified using concentrated hydrochloric acid. The organic layer was separated and successively washed with water and saturated brine, followed by drying with anhydrous sodium sulfate. After the solvent was distilled off under reduced pressure, the residue was purified by silica gel chromatography to obtain 74 mg (9%) of the title compound.

Workup

  1. temperatureunder reflux for 15 hours
  2. customThe organic layer was separated
  3. washsuccessively washed with water and saturated brine
  4. dry with materialby drying with anhydrous sodium sulfate
  5. distillationAfter the solvent was distilled off under reduced pressure
  6. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-28a9ebc1eb3a46569a2b5b92249059b1
Source dataset
uspto-grants-2014_07
Patent number
US08785631B2

Reaction notes

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