(2S)-2-[(1,2,3,3a,4,8b-Hexahydrocyclopenta[b]Indol-5-ylcarbonyl)Amino]-Propanoic Acid → (2S)-2-Methyl-2,3,8,9,10,10a-Hexahydro-7bH-Cyclopenta[b][1,4]Diazepino-[6,7,1-hi]Indole-1,4-Dione

HRID 2227738Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2227738
[CH2:1]1[CH:12]2[CH:4]([NH:5][C:6]3[C:7]([C:13]([NH:15][C@@H:16]([CH3:20])[C:17](O)=[O:18])=[O:14])=[CH:8][CH:9]=[CH:10][C:11]=32)[CH2:3][CH2:2]1>C(O)(=O)C>[CH3:20][C@@H:16]1[NH:15][C:13](=[O:14])[C:7]2=[C:6]3[C:11](=[CH:10][CH:9]=[CH:8]2)[CH:12]2[CH2:1][CH2:2][CH2:3][CH:4]2[N:5]3[C:17]1=[O:18]

Komponenten

3

Edukt 1

HCID 12132977(2S)-2-[(1,2,3,3a,4,8b-Hexahydrocyclopenta[b]Indol-5-ylcarbonyl)Amino]-Propanoic Acid

Produkt 1

HCID 69263029(2S)-2-Methyl-2,3,8,9,10,10a-Hexahydro-7bH-Cyclopenta[b][1,4]Diazepino-[6,7,1-hi]Indole-1,4-DioneAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A solution of (2S)-2-[(1,2,3,3a,4,8b-hexahydrocyclopenta[b]indol-5-ylcarbonyl)amino]propanoic acid (6.1 mmol, 1.6 g) was dissolved in acetic acid (50 mL) and heated to reflux for 18 h. The reaction was allowed to cool to room temperature and was concentrated to dryness. The crude material was purified by flash column chromatography (silica gel; 1:1 ethyl acetate-hexanes) to provide two diastereomers: less polar product (0.88 mmol, 0.23 g, 14%) and more polar product (0.18 mmol, 45 mg, 3%). The mixed fractions were also collected to provide another 3.9 mmol (1.0 g, 64%) of material.

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux for 18 h
  3. concentrationwas concentrated to dryness
  4. customThe crude material was purified by flash column chromatography (silica gel; 1:1 ethyl acetate-hexanes)
  5. customto provide two diastereomers
  6. customThe mixed fractions were also collected

Quellen und Nachweise

ORD-Eintrag
ord-fbff2e56d9454752ad927b938907f00c
Quelldatensatz
uspto-grants-2002_07
Patentnummer
US06414144B1

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