18-Crown-6 → HCID 22144650, 화합물

HRID 1825003

반응식

HRID 1825003 반응식
O1CCOCCOCCOCCOCCOCC1.CC(C)([O-])C.[K+].[CH3:25][C:26]([CH3:46])([CH3:45])[CH2:27][C:28]([NH:30][C:31]1[CH:32]=[C:33]2[C:37](=[CH:38][CH:39]=1)[NH:36][C:35]([C:40]([O:42][CH2:43][CH3:44])=[O:41])=[CH:34]2)=[O:29].[F:47][C:48]([F:58])([F:57])[C:49]1[CH:56]=[CH:55][CH:54]=[CH:53][C:50]=1[CH2:51]Br>C1COCC1>[CH3:25][C:26]([CH3:45])([CH3:46])[CH2:27][C:28]([NH:30][C:31]1[CH:32]=[C:33]2[C:37](=[CH:38][CH:39]=1)[N:36]([CH2:51][C:50]1[CH:53]=[CH:54][CH:55]=[CH:56][C:49]=1[C:48]([F:47])([F:57])[F:58])[C:35]([C:40]([O:42][CH2:43][CH3:44])=[O:41])=[CH:34]2)=[O:29]

참가 물질

6

반응물 4

HCID 2855718-Crown-6HCID 1230571-(Bromomethyl)-2-(trifluoromethyl)benzeneHCID 22144643Ethyl 5-[(3,3-dimethylbutanoyl)amino]-1H-indole-2-carboxylateHCID 23665647Potassium tert-butoxide

생성물 1

HCID 22144650HCID 22144650, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

Under argon, 35 mg (0.13 mmol) of 1,4,7,10,13,16-hexaoxacyclooctadecane (18-crown-6) are initially charged in 7 ml of THF, and 1.98 ml (1.98 mmol) of a 1-molar potassium tert-butoxide solution in THF and 400 mg (1.32 mmol) of ethyl 5-[(3,3-dimethylbutanoyl)amino]-1H-indole-2-carboxylate from Example LXII are added. The mixture is stirred at RT for 15 minutes and cooled to 0° C. A solution of 474 mg (1.98 mmol) of 2-trifluoromethylbenzyl bromide in 12 ml of THF is slowly added dropwise. The ice-bath is removed and the mixture stirred at RT for 1 hour. 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. The residue is purified by column chromatography (mobile phase: cyclohexane:ethyl acetate 5:1).

후처리

  1. temperaturecooled to 0° C
  2. customThe ice-bath is removed
  3. stirringthe mixture stirred at RT for 1 hour
  4. additionFor work-up, the mixture is diluted with water
  5. customthe THF is removed under reduced pressure
  6. customa rotary evaporator
  7. extractionThe aqueous residue is extracted with ethyl acetate
  8. washthe organic phase is washed with sat. sodium chloride solution
  9. dry with materialdried with sodium sulphate
  10. filtrationfiltered
  11. customdried under reduced pressure
  12. customThe residue is purified by column chromatography (mobile phase: cyclohexane:ethyl acetate 5:1)

출처 및 근거

ORD 기록
ord-365e2044aada4bb8b528b9fb25bf4409
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07045544B2

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