Trifluoroacetic acid → ethyl 5-methyl-1-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxylate

HRID 1748270노트

반응식

HRID 1748270 반응식
C(OC([NH:8][CH2:9][CH2:10][CH:11]([N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:20]=2)[CH:15]=[C:14]1[C:27](OCC)=[O:28])[CH3:12])=O)(C)(C)C.C(O)(C(F)(F)F)=O.C(N(CC)CC)C.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl.C(O)C>[CH3:12][CH:11]1[N:13]2[C:21]3[CH:20]=[C:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:18]=[CH:17][C:16]=3[CH:15]=[C:14]2[C:27](=[O:28])[NH:8][CH2:9][CH2:10]1

참가 물질

7

반응물 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 67236468diethyl 1-{4-[(tert-butoxycarbonyl)amino]butan-2-yl}-1H-indole-2,6-dicarboxylate

생성물 1

HCID 67235486ethyl 5-methyl-1-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxylate수율 59%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 6344Dichloromethane용매

실험 절차

To a solution of diethyl 1-{4-[(tert-butoxycarbonyl)amino]butan-2-yl}-1H-indole-2,6-dicarboxylate (1.04 g, 1.8 mmol) in CH2Cl2 (4 mL) is added TFA (4 mL). The reaction mixture is stirred for 1 h and the solvent is removed under vacuum. To a solution of the residue in ethanol (10 mL) is added triethylamine (0.75 mL, 5.4 mmol) and K2CO3 (742 mg, 5.4 mmol). The reaction mixture is refluxed for 3 h. Then the solvent is evaporated, the residue is partitioned between EtOAc and water. The organic layer is then separated, dried (MgSO4) and concentrated to afford crude compound which is purified by flash column chromatography to afford the title compound (300 mg, 59% for two steps).

후처리

  1. customthe solvent is removed under vacuum
  2. temperatureThe reaction mixture is refluxed for 3 h
  3. customThen the solvent is evaporated
  4. customthe residue is partitioned between EtOAc and water
  5. customThe organic layer is then separated
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customto afford crude compound which
  9. customis purified by flash column chromatography

출처 및 근거

ORD 기록
ord-43639a56a94a4e46a595ace36c56ff31
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09150577B2

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