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Trifluoroacetic acid → 5-(N-glycylamino)-2-phenyl-1,3,4,5-tetrahydrobenz[cd]indole

HRID 1637269
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HRID 1637269 반응식
C(OC([NH:8][CH2:9][C:10]([NH:12][CH:13]1[C:23]2[C:24]3[C:16](=[C:17]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[NH:18][C:19]=3[CH:20]=[CH:21][CH:22]=2)[CH2:15][CH2:14]1)=[O:11])=O)(C)(C)C.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>C(Cl)Cl>[NH2:8][CH2:9][C:10]([NH:12][CH:13]1[C:23]2[C:24]3[C:16](=[C:17]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[NH:18][C:19]=3[CH:20]=[CH:21][CH:22]=2)[CH2:15][CH2:14]1)=[O:11]
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참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 193482985-[N-(N-t-butoxycarbonylglycyl)amino]-2-phenyl-1,3,4,5-tetrahydrobenz[cd]indole

생성물 1

HCID 193483575-(N-glycylamino)-2-phenyl-1,3,4,5-tetrahydrobenz[cd]indole수율 41%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A portion (470 mg) of the crude compound obtained in Example 126 was suspended in methylene chloride (4 ml) and to the suspension was added trifluoroacetic acid (4 ml). The mixture was stirred for 1 hour at room temperature. The reaction mixture was made basic with saturated aqueous solution of sodium hydrogencarbonate and extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-ethyl acetate/methanol=9:1) to yield 100 mg (41%) of the titled compound.

후처리

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThen, the solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate-ethyl acetate/methanol=9:1)

출처 및 근거

ORD 기록
ord-3cf1cf431d5b482eb804bdc75085585f
출처 데이터셋
uspto-grants-2000_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06040331

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