Ammonia → 1,1-Diethyl-3-[13-(1,3-dithiolan-2-yl)-2,6-dimethyl-8alphaergolinyl]-urea

HRID 35850

Reaktionsgleichung

Reaktionsgleichung von HRID 35850
[CH2:1]([N:3]([CH2:25][CH3:26])[C:4]([NH:6][C@H:7]1[CH2:21][C@H:20]2[C@@H:10]([CH2:11][C:12]3[C:22]4[C:15](=[CH:16][CH:17]=[CH:18][C:19]2=4)[NH:14][C:13]=3[CH3:23])[N:9]([CH3:24])[CH2:8]1)=[O:5])[CH3:2].[CH:27]([SH:30])([SH:29])C.N.[CH2:32](OC=O)[CH3:33]>C(Cl)(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl.ClCCl.O.CO>[CH2:25]([N:3]([CH2:1][CH3:2])[C:4]([NH:6][C@H:7]1[CH2:21][C@H:20]2[C@@H:10]([CH2:11][C:12]3[C:22]4[C:15](=[CH:16][C:17]([CH:27]5[S:30][CH2:33][CH2:32][S:29]5)=[CH:18][C:19]2=4)[NH:14][C:13]=3[CH3:23])[N:9]([CH3:24])[CH2:8]1)=[O:5])[CH3:26]

Komponenten

10

Edukt 4

HCID 222AmmoniaHCID 8025Ethyl formateHCID 336451,1-EthanedithiolHCID 140110111,1-Diethyl-3-(2,6-dimethyl-8alpha-ergolinyl)urea

Produkt 1

HCID 867486521,1-Diethyl-3-[13-(1,3-dithiolan-2-yl)-2,6-dimethyl-8alphaergolinyl]-urea

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 24193Titanium TetrachlorideKatalysatorHCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 6212ChloroformLösungsmittel2×HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

5.31 g of 1,1-diethyl-3-(2,6-dimethyl-8alpha-ergolinyl)-urea (15 mmol) is dissolved in 150 ml of chloroform and 50 ml of formic acid ethyl ester, 2.8 ml of ethanedithiol (33 mmol) and 60 ml of a 1 molar solution of titanium tetrachloride in dichloromethane (60 mmol) are added and stirred for 20 hours at room temperature. Then, it is mixed with 40 ml of methanol and 300 ml of water, made alkaline with 30 ml of 25% ammonia solution and shaken out with dichloromethane. The organic phases are dried with sodium sulfate, concentrated by evaporation and the residue is chromatographed on silica gel with dichloromethane/methanol. 4.14 g of substance, which crystallizes from ethyl acetate, is isolated, [α]D =-4° (0.5 % in chloroform).

Aufarbeitung

  1. dry with materialThe organic phases are dried with sodium sulfate
  2. concentrationconcentrated by evaporation
  3. customthe residue is chromatographed on silica gel with dichloromethane/methanol
  4. custom4.14 g of substance, which crystallizes from ethyl acetate
  5. customis isolated

Quellen und Nachweise

ORD-Eintrag
ord-fa9675f3aadc48238365a85657fbe7e7
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05411966

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