L-Methionine → N-[[1-[(2-Benzothienylcarbonyl)amino]cyclohexyl]carbonyl]-L-methionine

HRID 1627496Notes

Reaction equation

HRID 1627496 reaction equation
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH2:4][S:5][CH3:6].[S:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[CH:12]=[C:11]1[C:19]1[O:23][C:22](=[O:24])[C:21]2([CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)[N:20]=1>CN1CCOCC1>[S:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[CH:12]=[C:11]1[C:19]([NH:20][C:21]1([C:22]([NH:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH2:4][S:5][CH3:6])=[O:24])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)=[O:23]

Participants

4

Reactant 2

HCID 6137L-MethionineHCID 576728542-(2-Benzothienyl)-3-oxa-1-azaspiro[4.5]dec-1-en-4-one

Product 1

HCID 24738022N-[[1-[(2-Benzothienylcarbonyl)amino]cyclohexyl]carbonyl]-L-methionineYield 22.4%

Reagents, catalysts & solvents 1

HCID 79724-MethylmorpholineSolvent

Procedure

10 ml of N-methylmorpholine was added to 522 mg (3.5 mmol) of L-methionine and 500 mg (1.75 mmol) of 2-(2-benzothienyl)-3-oxa-1-azaspiro[4.5]dec-1-en-4-one, and the mixture was stirred and heated under reflux overnight. The reaction solution was distilled off under reduced pressure, a 10% aqueous potassium hydrogensulfate solution was added thereto, and the mixture was extracted with methylene chloride three times. The obtained organic layer was dried with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. Ethyl acetate was added to the obtained residue, and the mixture was stirred overnight. The precipitated solid was collected by filtration and dried under reduced pressure to obtain 170 mg (22%) of the title compound.

Workup

  1. temperatureheated
  2. temperatureunder reflux overnight
  3. distillationThe reaction solution was distilled off under reduced pressure
  4. additiona 10% aqueous potassium hydrogensulfate solution was added
  5. extractionthe mixture was extracted with methylene chloride three times
  6. dry with materialThe obtained organic layer was dried with anhydrous sodium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. additionEthyl acetate was added to the obtained residue
  9. stirringthe mixture was stirred overnight
  10. filtrationThe precipitated solid was collected by filtration
  11. customdried under reduced pressure

Sources & evidence

ORD record
ord-a4d278ef7b974fcc83d22368e5ca7270
Source dataset
uspto-grants-2014_07
Patent number
US08785631B2

Reaction notes

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