18-Crown-6 → HCID 23573456, 화합물

HRID 1824991노트

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HRID 1824991 반응식
O1CCOCCOCCOCCOCCOCC1.CC(C)([O-])C.[K+].[N+:25]([C:28]1[CH:29]=[C:30]2[C:34](=[CH:35][CH:36]=1)[NH:33][C:32]([C:37]([NH:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:38])=[CH:31]2)([O-:27])=[O:26].Br[CH2:47][C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49]>ClCCl.C1COCC1>[NH:39]([C:37]([C:32]1[N:33]([CH2:47][C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49])[C:34]2[C:30]([CH:31]=1)=[CH:29][C:28]([N+:25]([O-:27])=[O:26])=[CH:36][CH:35]=2)=[O:38])[C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1

참가 물질

7

반응물 4

HCID 2855718-Crown-6HCID 79177tert-Butyl bromoacetateHCID 135231415-nitro-N-phenyl-1H-indole-2-carboxamideHCID 23665647Potassium tert-butoxide

생성물 1

HCID 23573456HCID 23573456, 화합물

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매2회

실험 절차

Under argon, 328 mg (1.24 mmol) of 1,4,7,10,13,16-hexaoxacyclooctadecane (18-crown-6) are initially charged in 61 ml of dichloromethane, and 15 ml (14.93 mmol) of a 1-molar potassium tert-butoxide solution in THF and 3.50 g (12.44 mmol) of 5-nitro-N-phenyl-1H-indole-2-carboxamide from Example XLVIII are added. The mixture is stirred at RT for 15 minutes and then cooled to. 0° C. A solution of 3.64 g (18.67 mmol) of tert-butyl bromoacetate in 100 ml of THF is slowly added dropwise. The ice-bath is removed and the mixture is stirred at RT overnight. For work-up, the mixture is diluted with water and the THF is removed under reduced pressure using a rotary evaporator. The aqueous residue is extracted with ethyl acetate and the organic phase is washed with sat. sodium chloride solution, dried with sodium sulphate, filtered and dried under reduced pressure.

후처리

  1. temperaturecooled to
  2. custom0° C
  3. customThe ice-bath is removed
  4. stirringthe mixture is stirred at RT overnight
  5. additionFor work-up, the mixture is diluted with water
  6. customthe THF is removed under reduced pressure
  7. customa rotary evaporator
  8. extractionThe aqueous residue is extracted with ethyl acetate
  9. washthe organic phase is washed with sat. sodium chloride solution
  10. dry with materialdried with sodium sulphate
  11. filtrationfiltered
  12. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-d52a461cc5a246a4bd129ca0ceb20c0d
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07045544B2

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