L-Methionine → N-[[1-[[(4-Methoxyphenyl)carbonyl]amino]cyclohexyl]carbonyl]-L-methionine

HRID 1627497Notes

Reaction equation

HRID 1627497 reaction equation
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH2:4][S:5][CH3:6].[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[O:22][C:21](=[O:23])[C:20]3([CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)[N:19]=2)=[CH:14][CH:13]=1>CN1CCOCC1>[CH3:10][O:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]([NH:19][C:20]2([C:21]([NH:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH2:4][S:5][CH3:6])=[O:23])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]2)=[O:22])=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 6137L-MethionineHCID 576728572-(4-Methoxyphenyl)-3-oxa-1-azaspiro[4.5]dec-1-en-4-one

Product 1

HCID 24738018N-[[1-[[(4-Methoxyphenyl)carbonyl]amino]cyclohexyl]carbonyl]-L-methionineYield 13%

Reagents, catalysts & solvents 1

HCID 79724-MethylmorpholineSolvent

Procedure

10 ml of N-methylmorpholine was added to 298 mg (2 mmol) of L-methionine and 259 mg (1 mmol) of 2-(4-methoxyphenyl)-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 hydrogensulfate, 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 52 mg (13%) 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 hydrogensulfate
  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-8c854bca5d624546a5e6798c7aa8479f
Source dataset
uspto-grants-2014_07
Patent number
US08785631B2

Reaction notes

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