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

HRID 73875Notes

Reaction equation

HRID 73875 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 heated under reflux 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, followed by drying with anhydrous sodium sulfate. After the solvent was distilled off under reduced pressure, diethyl ether was added, 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 heated
  2. temperatureunder reflux 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 materialby drying 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-db544b68519545c5a2c8df77955edff4
Source dataset
uspto-grants-2014_09
Patent number
US08829209B2

Reaction notes

Loading…