HCID 13908798, 화합물 → (2'S,3S,4'Z,6'S)-6-bromo-2'-(3-chlorophenyl)-4'-hydroxyimino-6'-prop-1-en-2-ylspiro[1H-indole-3,1'-cyclohexane]-2-one

HRID 1987801노트

반응식

HRID 1987801 반응식
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]3([CH:16]([C:17]([CH3:19])=[CH2:18])[CH2:15][C:14](=O)[CH2:13][CH:12]3[C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=3)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[OH-:28].[NH4+:29].Cl>CCO.O>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C@@:6]3([C@H:16]([C:17]([CH3:19])=[CH2:18])[CH2:15]/[C:14](=[N:29]/[OH:28])/[CH2:13][C@H:12]3[C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=3)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 13908798HCID 13908798, 화합물HCID 68904372rac-(1S,2S,6R)-6'-bromo-2-(3-chlorophenyl)-6-isopropenyl spiro[cyclohexane-1,3'-[3H]indole]-2',4(1'H)-dione

생성물 1

HCID 140531877(2'S,3S,4'Z,6'S)-6-bromo-2'-(3-chlorophenyl)-4'-hydroxyimino-6'-prop-1-en-2-ylspiro[1H-indole-3,1'-cyclohexane]-2-one수율 75.3%

시약·촉매·용매 1

HCID 19096565Water ethanol용매

실험 절차

The suspension of rac-(1S,2S,6R)-6′-bromo-2-(3-chlorophenyl)-6-isopropenyl spiro[cyclohexane-1,3′-[3H]indole]-2′,4(1′H)-dione (0.23 g, 0.52 mmol) and NH4OH—HCl (0.1 g, 0.52 mmol) in EtOH-water (3/2, 20 mL) was allowed to reflux for 1 h. TLC analysis indicated the formation of desired product and complete consumption of starting material. The reaction was cooled to room temperature, and water was added. The mixture was extracted with ethyl acetate. The organic layer was separated, dried over MgSO4, and concentrated. The residue was purified by chromatography (EtOAc:hexanes=1:2, then 1:1) to give the title compound as a white solid (0.18 g, 75%): HRMS (ES+) m/z Calcd for C22H20BrClN2O2+H [(M+H)+]: 459.0470, Found: 459.0470.

후처리

  1. temperatureto reflux for 1 h
  2. customthe formation of desired product and complete consumption of starting material
  3. additionwater was added
  4. extractionThe mixture was extracted with ethyl acetate
  5. customThe organic layer was separated
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography (EtOAc

출처 및 근거

ORD 기록
ord-e626ec31474d466fb7e6a5543b68a760
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07553833B2

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