Ethyl isocyanate → HCID 86752673, Verbindung

HRID 1292393Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1292393
[CH2:1]([O:8][C:9](=[O:49])[N:10]([CH2:31][CH2:32][CH2:33][CH2:34][C:35]1[CH:40]=[CH:39][C:38]([O:41][CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)=[CH:37][CH:36]=1)[CH2:11][CH2:12][C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([OH:22])[CH:20]=2)[NH:15][C:14]=1[C:23]1[CH:28]=[C:27]([CH3:29])[CH:26]=[C:25]([CH3:30])[CH:24]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:50]([N:52]=[C:53]=[O:54])[CH3:51]>>[CH2:1]([O:8][C:9]([N:10]([CH2:31][CH2:32][CH2:33][CH2:34][C:35]1[CH:40]=[CH:39][C:38]([O:41][CH2:42][C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)=[CH:37][CH:36]=1)[CH2:11][CH2:12][C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([O:22][C:53](=[O:54])[NH:52][CH2:50][CH3:51])[CH:20]=2)[NH:15][C:14]=1[C:23]1[CH:24]=[C:25]([CH3:30])[CH:26]=[C:27]([CH3:29])[CH:28]=1)=[O:49])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

3

Edukt 2

HCID 8022Ethyl isocyanate2×HCID 70227002HCID 70227002, Verbindung

Produkt 1

HCID 86752673HCID 86752673, Verbindung

Versuchsvorschrift

To a solution of [4-(4-benzyloxyphenyl)-butyl]-[2-[2-(3,5-dimethylphenyl)-5-hydroxy-1H-indol-3-yl]ethyl]carbamic acid benzyl ester (50 mg in 0.5 mL dry tetrahydrofuran) was added 0.035 mL of ethyl isocyanate and the mixture stirred at room temperature. Over the course of 2 weeks, additional ethyl isocyanate was added in portions and the mixture heated to reflux for several days after which time it was cooled to room temperature, concentrated in vacuo and purified by flash chromatography on silica gel (hexane:ethyl acetate, 2:1) to give the title compound (20 mg).

Aufarbeitung

  1. temperaturethe mixture heated
  2. temperatureto reflux for several days after which time it
  3. temperaturewas cooled to room temperature
  4. concentrationconcentrated in vacuo
  5. custompurified by flash chromatography on silica gel (hexane:ethyl acetate, 2:1)

Quellen und Nachweise

ORD-Eintrag
ord-53290def764c41fcaab29989505d1493
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05756507

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