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3-Chloropropanesulphonyl chloride → 3-(3-Chloropropylsulfonylamino)-2-methoxy-1-octadecylcarbamoyloxypropane

HRID 846965
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HRID 846965 반응식
[CH3:1][O:2][CH:3]([CH2:6][O:7][C:8](=[O:28])[NH:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:4][NH2:5].[Cl:29][CH2:30][CH2:31][CH2:32][S:33](Cl)(=[O:35])=[O:34]>ClCCl.C(N(CC)CC)C>[Cl:29][CH2:30][CH2:31][CH2:32][S:33]([NH:5][CH2:4][CH:3]([O:2][CH3:1])[CH2:6][O:7][C:8](=[O:28])[NH:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])(=[O:35])=[O:34]
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참가 물질

5

반응물 2

HCID 154103-Chloropropanesulphonyl chlorideHCID 149922622-Methoxy-3-octadecylcarbamoyloxypropylamine

생성물 1

HCID 148350183-(3-Chloropropylsulfonylamino)-2-methoxy-1-octadecylcarbamoyloxypropane수율 91.2%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8471Triethylamine용매

실험 절차

To a solution of 3.368 g (10.22 mM) of 3-hexadecyloxy-2-methoxypropylamine IV a3 in 35 ml of dichloromethane and 1.85 ml (13.29 mM) of triethylamine is added 1.99 g (11.24 mM) of 3-chloropropanesulfonyl chloride with ice-cooling and the mixture is stirred at room temperature for 4 hours and then heated for 30 minutes with stirring. After the solvent is evaporated, the residue is purified by the column chromatography on silica gel with a n-hexane-ethyl acetate (3:1) mixture as an eluent. The product is recrystallized form methanol to give 4.15 g (8.827 mM) of 3-(3-chloropropylsulfonylamino)-1-hexadecyloxy-2-methoxypropane III a3 as a colorless powder in 86% yield.

후처리

  1. temperaturecooling
  2. temperatureheated for 30 minutes
  3. stirringwith stirring
  4. customAfter the solvent is evaporated
  5. customthe residue is purified by the column chromatography on silica gel with a n-hexane-ethyl acetate (3:1) mixture as an eluent
  6. customThe product is recrystallized form methanol

출처 및 근거

ORD 기록
ord-3707731488b04e08bef4d21bccacbb69
출처 데이터셋
uspto-grants-1992_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05138067

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