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Water → 1-[6-(N-tert-Butoxycarbonylamino)-1-hexyl]-1,2,3,4-tetrahydroquinoline-2-one

HRID 555325
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HRID 555325 반응식
C[Si]([N-][Si](C)(C)C)(C)C.[K+].[O:11]=[C:12]1[CH2:21][CH2:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13]1.[C:22]([O:26][C:27]([NH:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]Br)=[O:28])([CH3:25])([CH3:24])[CH3:23].O>C1(C)C=CC=CC=1.O1CCCC1>[C:22]([O:26][C:27]([NH:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][N:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:20][CH2:21][C:12]1=[O:11])=[O:28])([CH3:25])([CH3:24])[CH3:23]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 962WaterHCID 64796HydrocarbostyrilHCID 3251421Potassium bis(trimethylsilyl)amideHCID 16211353tert-Butyl (6-bromohexyl)carbamate

생성물 1

HCID 669882961-[6-(N-tert-Butoxycarbonylamino)-1-hexyl]-1,2,3,4-tetrahydroquinoline-2-one

시약·촉매·용매 2

HCID 1140Toluene
용매
HCID 8028Tetrahydrofuran용매2회

실험 절차

0.5M Potassium bis-(trimethylsilyl)-amide in toluene (10 ml) was added dropwise at −30° C. in an argon atmosphere to a stirred solution of 2-oxo-1,2,3,4-tetrahydroquinoline (735 mg) in tetrahydrofuran (50 ml). After further cooling to −50° C. a solution of N-(tert-butoxycarbonyl)-6-bromo-hexylamine (1.5 g) in tetrahydrofuran (10 ml) was added slowly. Subsequently the temperature was allowed to raise to room temperature followed by heating at 50-60° C. for 48 hours. Ice and water were added and the mixture was extracted twice with ethyl acetate. The organic phases were washed with saturated sodium chloride, dried and evaporated to leave a yellow oil which after purification by chromatography on silica gel with ethyl acetate/hexane (1:1) as eluent gave the desired compound as a colourless oil.

후처리

  1. additionwas added slowly
  2. temperatureby heating at 50-60° C. for 48 hours
  3. extractionthe mixture was extracted twice with ethyl acetate
  4. washThe organic phases were washed with saturated sodium chloride
  5. customdried
  6. customevaporated
  7. customto leave a yellow oil which
  8. customafter purification by chromatography on silica gel with ethyl acetate/hexane (1:1) as eluent

출처 및 근거

ORD 기록
ord-755de4918fee4d9aa5ce21b2aa2929dd
출처 데이터셋
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08053446B2

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