methyl 5-[(2R)-2-aminopropyl]-1H-indole-2-carboxylate → methyl 5-{(2R)-2-[((2R)-2-[4-(benzyloxy)-3-(hydroxymethyl)phenyl]-2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)amino]propyl}-1H-indole-2-carboxylate

HRID 1760716노트

반응식

HRID 1760716 반응식
[NH2:1][C@H:2]([CH3:17])[CH2:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([C:13]([O:15][CH3:16])=[O:14])=[CH:7]2.[CH2:18]([O:25][C:26]1[CH:31]=[CH:30][C:29]([C@@H:32]([O:35][Si:36]([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:38])[CH3:37])[CH2:33]Br)=[CH:28][C:27]=1[CH2:43][OH:44])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>ClCCl>[NH3:1].[CH2:18]([O:25][C:26]1[CH:31]=[CH:30][C:29]([C@@H:32]([O:35][Si:36]([C:39]([CH3:41])([CH3:40])[CH3:42])([CH3:37])[CH3:38])[CH2:33][NH:1][C@H:2]([CH3:17])[CH2:3][C:4]2[CH:5]=[C:6]3[C:10](=[CH:11][CH:12]=2)[NH:9][C:8]([C:13]([O:15][CH3:16])=[O:14])=[CH:7]3)=[CH:28][C:27]=1[CH2:43][OH:44])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

참가 물질

5

반응물 2

HCID 12988833methyl 5-[(2R)-2-aminopropyl]-1H-indole-2-carboxylateHCID 12988834[2-(benzyloxy)-5-((1R)-2-bromo-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)phenyl]methanol

생성물 2

HCID 222AmmoniaHCID 12988832methyl 5-{(2R)-2-[((2R)-2-[4-(benzyloxy)-3-(hydroxymethyl)phenyl]-2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)amino]propyl}-1H-indole-2-carboxylate수율 60.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A solution of methyl 5-[(2R)-2-aminopropyl]-1H-indole-2-carboxylate (Preparation 14, 5.00 g, 21.5 mmol) and [2-(benzyloxy)-5-((1R)-2-bromo-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)phenyl]methanol (Preparation 20, 4.86 g, 10.8 mmol) in dichloromethane (50 ml) was heated to 90° C. allowing the dichloromethane to evaporate gradually. The resulting melt was left at 90° C. for 16 h under nitrogen. The reaction mixture was then cooled to room temperature and the resulting solid triturated with dichloromethane. The solid was filtered off and the solvent removed in vacuo to give a pale orange oil. The residue was purified by flash column chromatography on silica gel eluting with dichloromethane:methanol:0.88 ammonia (99:1:0.1 by volume) to give the title compound as a pale yellow oil (3.90 g).

후처리

  1. customto evaporate gradually
  2. customthe resulting solid triturated with dichloromethane
  3. filtrationThe solid was filtered off
  4. customthe solvent removed in vacuo
  5. customto give a pale orange oil
  6. customThe residue was purified by flash column chromatography on silica gel eluting with dichloromethane

출처 및 근거

ORD 기록
ord-c2f9a13640904af1821f0568fd0d292e
출처 데이터셋
uspto-grants-2005_01
특허 번호
US06844362B2

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