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Triethylamine → 2-[3-(N,N-diethylamino)-2-hydroxypropylaminocarbonyl]-3-pivaloyloxy-1-phenylindole hydrochloride

HRID 1194396
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HRID 1194396 반응식
Cl.[CH2:2]([N:4]([CH2:7][CH:8]([OH:29])[CH2:9][NH:10][C:11]([C:13]1[N:14]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:15]2[C:20]([C:21]=1[OH:22])=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH2:5][CH3:6])[CH3:3].C(N(CC)CC)C.[C:37]([Cl:43])(=[O:42])[C:38]([CH3:41])([CH3:40])[CH3:39]>C(Cl)Cl>[ClH:43].[CH2:2]([N:4]([CH2:7][CH:8]([OH:29])[CH2:9][NH:10][C:11]([C:13]1[N:14]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:15]2[C:20]([C:21]=1[O:22][C:37](=[O:42])[C:38]([CH3:41])([CH3:40])[CH3:39])=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH2:5][CH3:6])[CH3:3]
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반응물 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 547241132-[3-(N,N-diethylamino)-2-hydroxypropylaminocarbonyl]-3-hydroxy-1-phenylindole hydrochloride

생성물 1

HCID 212700882-[3-(N,N-diethylamino)-2-hydroxypropylaminocarbonyl]-3-pivaloyloxy-1-phenylindole hydrochloride

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

12.6 g of 2-[3-(N,N-diethylamino)-2-hydroxypropylaminocarbonyl]-3-hydroxy-1-phenylindole hydrochloride (0.03 mole) are mixed with 150 ml of methylene chloride, 4.2 ml of triethylamine (0.03 mole) and 3.9 ml of pivaloyl chloride (0.03 mole) and the reaction mixture allowed to stand for 3 h at room temperature. The mixture is subsequently washed with a saturated sodium chloride solution, dried over sodium sulfate and filtered. The solution is then evaporated, the residue dissolved in methylene chloride and purified by means of low pressure chromatography over silica gel acid. As the elution agent, first methylene chloride and subsequently methylene chloride containing 10% methanol are used. The 2-[3-(N,N-diethylamino)-2-hydroxypropylaminocarbonyl]-3-pivaloyloxy-1-phenylindole hydrochloride obtained as the residue after the evaporation of the eluate is then recrystallized from isopropanol. Melting point: 157°-159°.

후처리

  1. washThe mixture is subsequently washed with a saturated sodium chloride solution
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. customThe solution is then evaporated
  5. dissolutionthe residue dissolved in methylene chloride
  6. custompurified by means of low pressure chromatography over silica gel acid

출처 및 근거

ORD 기록
ord-97a787a7b6c042178a5e5b82744b7129
출처 데이터셋
uspto-grants-1989_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04814345

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