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Water → 5-[N-(N-t-butoxycarbonylglycyl)amino]-2-phenyl-1,3,4,5-tetrahydrobenz[cd]indole

HRID 1637268
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HRID 1637268 반응식
[NH2:1][CH:2]1[C:12]2[C:13]3[C:5](=[C:6]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[NH:7][C:8]=3[CH:9]=[CH:10][CH:11]=2)[CH2:4][CH2:3]1.[C:20]([O:24][C:25]([NH:27][CH2:28][C:29](O)=[O:30])=[O:26])([CH3:23])([CH3:22])[CH3:21].ClC(Cl)CCCCCN=C=N.O>C(Cl)Cl>[C:20]([O:24][C:25]([NH:27][CH2:28][C:29]([NH:1][CH:2]1[C:12]2[C:13]3[C:5](=[C:6]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[NH:7][C:8]=3[CH:9]=[CH:10][CH:11]=2)[CH2:4][CH2:3]1)=[O:30])=[O:26])([CH3:23])([CH3:22])[CH3:21]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 962WaterHCID 78288N-(tert-butoxycarbonyl)glycineHCID 101988185-Amino-2-phenyl-1,3,4,5-tetrahydrobenz[cd]indoleHCID 71510291Dichlorohexylcarbodiimide

생성물 1

HCID 193482985-[N-(N-t-butoxycarbonylglycyl)amino]-2-phenyl-1,3,4,5-tetrahydrobenz[cd]indole수율 143.9%

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

실험 절차

A portion (200 mg) of the compound obtained in Example 81 and N-t-butoxycarbonylglycine (170 mg) were suspended in methylene chloride (15 ml) and to the suspension was added dichlorohexylcarbodiimide (216 mg) under cooling with ice. The mixture was stirred for 1 hour at room temperature. To the reaction mixture was added water, followed by extraction 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 to yield the titled compound (470 mg) as a crude yellow solid. The compound was used in the subsequent reaction without further purification.

후처리

  1. temperatureunder cooling with ice
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with water and saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThen, the solvent was distilled off under reduced pressure

출처 및 근거

ORD 기록
ord-dcc4a09ac9b04152b0917aa97b9017e5
출처 데이터셋
uspto-grants-2000_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06040331

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