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

HRID 35850

反応式

HRID 35850 の反応式
[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]

参加物

10

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 5

HCID 24193Titanium Tetrachloride触媒HCID 887Methanol溶媒HCID 962Water溶媒HCID 6212Chloroform溶媒2 回HCID 6344Dichloromethane溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-fa9675f3aadc48238365a85657fbe7e7
出典データセット
uspto-grants-1995_05
特許番号
US05411966

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