Diisopropylethylamine → N-[[1-[(2-Benzothienylcarbonyl)amino]cyclohexyl]carbonyl]-L-methionine methyl ester

HRID 1851855Notes

Reaction equation

HRID 1851855 reaction equation
C(N(C(C)C)CC)(C)C.Cl.[CH3:11][O:12][C:13](=[O:20])[C@H:14]([CH2:16][CH2:17][S:18][CH3:19])[NH2:15].[S:21]1[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[CH:23]=[C:22]1[C:30]1[O:34][C:33](=[O:35])[C:32]2([CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]2)[N:31]=1>C1(C)C=CC=CC=1>[CH3:11][O:12][C:13](=[O:20])[C@H:14]([CH2:16][CH2:17][S:18][CH3:19])[NH:15][C:33]([C:32]1([NH:31][C:30]([C:22]2[S:21][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=3[CH:23]=2)=[O:34])[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40]1)=[O:35]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 11435579L-Methionine, methyl ester, hydrochlorideHCID 576728542-(2-Benzothienyl)-3-oxa-1-azaspiro[4.5]dec-1-en-4-one

Product 1

HCID 24739315N-[[1-[(2-Benzothienylcarbonyl)amino]cyclohexyl]carbonyl]-L-methionine methyl esterYield 86.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

679 mg (5.3 mmol) of diisopropylethylamine was added to a suspension of 419 mg (2 mmol) of L-methionine methyl ester hydrochloride and 500 mg (1.75 mmol) of 2-(2-benzothienyl)-3-oxa-1-azaspiro[4.5]dec-1-en-4-one in 10 ml of toluene, and the mixture was refluxed under heating overnight. After the solvent was distilled off under reduced pressure, ethyl acetate was added thereto, and the mixture was washed with a 10% aqueous potassium hydrogensulfate solution and saturated brine and dried with anhydrous sodium sulfate. After the solvent was distilled off under reduced pressure, diethyl ether was added thereto, and the mixture was stirred overnight. The precipitated solid was collected by filtration and dried under reduced pressure to obtain 678 mg (86%) of the title compound.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating overnight
  3. distillationAfter the solvent was distilled off under reduced pressure, ethyl acetate
  4. additionwas added
  5. washthe mixture was washed with a 10% aqueous potassium hydrogensulfate solution and saturated brine
  6. dry with materialdried with anhydrous sodium sulfate
  7. distillationAfter the solvent was distilled off under reduced pressure, diethyl ether
  8. additionwas added
  9. filtrationThe precipitated solid was collected by filtration
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-14430f640a044f70b3ccbfdabc46e17a
Source dataset
uspto-grants-2015_02
Patent number
US08957205B2

Reaction notes

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