1-Aminocyclohexanecarboxylic acid → 2-Cyclopentyl-3-oxa-1-azaspiro[4.5]dec-1-en-4-one

HRID 73841

반응식

HRID 73841 반응식
[CH:1]1([C:6](Cl)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:9][C:10]1([C:16](O)=[O:17])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.C(=O)([O-])[O-].[Na+].[Na+].Cl.C(N=C=NCCCN(C)C)C>C(OCC)(=O)C.O>[CH:1]1([C:6]2[O:7][C:16](=[O:17])[C:10]3([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]3)[N:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

참가 물질

7

반응물 4

HCID 13661-Aminocyclohexanecarboxylic acidHCID 10340Sodium CarbonateHCID 78284Cyclopentanecarbonyl chlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

생성물 1

HCID 247401222-Cyclopentyl-3-oxa-1-azaspiro[4.5]dec-1-en-4-one수율 42.5%

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매2회

실험 절차

1.98 g (15 mmol) of cyclopentanecarbonyl chloride was added to a solution of 2.16 g (15 mmol) of 1-aminocyclohexanecarboxylic acid and 4.8 g (45 mmol) of sodium carbonate in 50 ml of ethyl acetate-50 ml of water under ice-cooling. After the mixture was stirred at room temperature overnight, ethyl acetate was added thereto, and the mixture was washed with a 10% aqueous potassium hydrogensulfate solution, a saturated aqueous sodium bicarbonate solution and then saturated brine. After the obtained organic layer was washed with saturated brine, it was dried with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, methylene chloride was added thereto, and under ice-cooling, 1.59 g (8.3 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride was added. After the mixture was stirred at room temperature overnight, under reduced pressure, the reaction solution was concentrated, ethyl acetate was added thereto, and the mixture was successively washed with water, a 10% aqueous potassium hydrogensulfate solution, a saturated aqueous sodium hydrogencarbonate solution and saturated brine, followed by drying with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 1.41 g (42%) of the title compound.

후처리

  1. temperaturecooling
  2. washthe mixture was washed with a 10% aqueous potassium hydrogensulfate solution
  3. washAfter the obtained organic layer was washed with saturated brine, it
  4. dry with materialwas dried with anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure, methylene chloride
  6. additionwas added
  7. temperatureunder ice-cooling
  8. stirringAfter the mixture was stirred at room temperature overnight, under reduced pressure
  9. concentrationthe reaction solution was concentrated
  10. additionethyl acetate was added
  11. washthe mixture was successively washed with water
  12. dry with materialby drying with anhydrous sodium sulfate
  13. distillationThe solvent was distilled off under reduced pressure

출처 및 근거

ORD 기록
ord-bce3cbce48a14e97a14fd7c56094ad70
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829209B2

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