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

HRID 448788Notes

Reaction equation

HRID 448788 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, it was successively washed with water and saturated brine, and dried with anhydrous sodium sulfate. After the solvent was distilled off under reduced pressure, it 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. washit was successively washed with water and saturated brine
  4. dry with materialdried with anhydrous sodium sulfate
  5. distillationAfter the solvent was distilled off under reduced pressure, it
  6. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-5e5537546022424d899ad03faef2338e
Source dataset
uspto-grants-2013_07
Patent number
US08481725B2

Reaction notes

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