Diisopropylethylamine → N-[[1-[(2-Furanylcarbonyl)amino]cyclohexyl]carbonyl]-L-valinol

HRID 73845

반응식

HRID 73845 반응식
C(N(CC)C(C)C)(C)C.[NH2:10][C@H:11]([CH2:15][OH:16])[CH:12]([CH3:14])[CH3:13].[O:17]1[CH:21]=[CH:20][CH:19]=[C:18]1[C:22]1[O:26][C:25](=[O:27])[C:24]2([CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)[N:23]=1>C(Cl)Cl.C1(C)C=CC=CC=1>[O:17]1[CH:21]=[CH:20][CH:19]=[C:18]1[C:22]([NH:23][C:24]1([C:25]([NH:10][C@H:11]([CH2:15][OH:16])[CH:12]([CH3:14])[CH3:13])=[O:27])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1)=[O:26]

참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 640993L-ValinolHCID 247399602-(2-Furanyl)-3-oxa-1-azaspiro[4.5]dec-1-en-4-one

생성물 1

HCID 24876087N-[[1-[(2-Furanylcarbonyl)amino]cyclohexyl]carbonyl]-L-valinol수율 74.7%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 6344Dichloromethane용매

실험 절차

A solution of 8.81 ml (50.6 mmol) of N,N-diisopropylethylamine and 2.09 g (20.2 mmol) of L-valinol in 10 mL of methylene chloride was added to a solution of 3.71 g (16.9 mmol) of 2-(2-furanyl)-3-oxa-1-azaspiro[4.5]dec-1-en-4-one in 100 ml of toluene, and the mixture was heated under reflux for 14 hours. The reaction solution was concentrated under reduced pressure, ethyl acetate was added to the residue, and the mixture was washed with water, a 10% aqueous potassium hydrogensulfate solution, a saturated aqueous sodium hydrogencarbonate solution and then saturated brine. The organic layer was dried with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. Ethyl acetate was added to the residue, and the mixture was stirred overnight. The obtained crystal was collected by filtration to obtain 4.06 g (74.7%) of the title compound.

후처리

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 14 hours
  3. concentrationThe reaction solution was concentrated under reduced pressure, ethyl acetate
  4. additionwas added to the residue
  5. washthe mixture was washed with water
  6. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. additionEthyl acetate was added to the residue
  9. filtrationThe obtained crystal was collected by filtration

출처 및 근거

ORD 기록
ord-6405efd6ebeb41a4b29260cd120c5ea8
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829209B2

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