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

HRID 35850

반응식

HRID 35850 반응식
[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]

참가 물질

10

반응물 4

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

생성물 1

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

시약·촉매·용매 5

HCID 24193Titanium Tetrachloride촉매HCID 887Methanol용매HCID 962Water용매HCID 6212Chloroform용매2회HCID 6344Dichloromethane용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-fa9675f3aadc48238365a85657fbe7e7
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05411966

연결된 노트

불러오는 중…