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Ammonia → 3-[9,10-Didehydro-2-(1,3-dithiolan-2-yl)-6-methyl-8alpha-ergolinyl]-1,1-diethylurea

HRID 231713
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HRID 231713 반응식
[CH3:1][N:2]1[C@H:16]2[C:6]([C:7]3[CH:8]=[CH:9][CH:10]=[C:11]4[C:17]=3[C:14]([CH2:15]2)=[CH:13][NH:12]4)=[CH:5][C@H:4]([NH:18][C:19](=[O:25])[N:20]([CH2:23][CH3:24])[CH2:21][CH3:22])[CH2:3]1.C(O[CH2:29][CH3:30])=O.[CH:31]([SH:34])([SH:33])C.N>C(Cl)(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl.O.CO>[S:33]1[CH2:30][CH2:29][S:34][CH:31]1[C:13]1[NH:12][C:11]2[C:17]3[C:14]=1[CH2:15][C@@H:16]1[C:6]([C:7]=3[CH:8]=[CH:9][CH:10]=2)=[CH:5][C@H:4]([NH:18][C:19](=[O:25])[N:20]([CH2:23][CH3:24])[CH2:21][CH3:22])[CH2:3][N:2]1[CH3:1]
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참가 물질

9

반응물 4

HCID 222AmmoniaHCID 8025Ethyl formateHCID 28864LisurideHCID 336451,1-Ethanedithiol

생성물 1

HCID 867420553-[9,10-Didehydro-2-(1,3-dithiolan-2-yl)-6-methyl-8alpha-ergolinyl]-1,1-diethylurea수율 12%

시약·촉매·용매 4

HCID 24193
Titanium Tetrachloride
촉매
HCID 887Methanol용매
HCID 962Water용매
HCID 6212Chloroform용매2회

실험 절차

Under argon, 11.5 g (0.03 mol) of 3-(9,10-didehydro-6-methyl-8α-ergolinyl)-1,1-diethylurea is dissolved in 300 ml of chloroform. At room temperature, 105 ml of ethyl formate and 5.4 ml of ethanedithiol are added in succession. Then 13.2 ml of titanium(IV) chloride in 150 ml of chloroform is added dropwise. The mixture is agitated for 3 days at room temperature. To work up the mixture, it is cooled in an ice bath and 75 ml of methanol and 600 ml of water are added in sequence dropwise to this mixture. The solution is rendered alkaline with 60 ml of 25% ammonia solution and extracted with methylene chloride. The organic phases are washed with water and dried over magnesium sulfate. The concentrated residue is chromatographed under pressure on silica gel with ethyl acetate/methanol 95:5, thus isolating 1.7 g of 3-[9,10-didehydro-2-(1,3-dithiolan-2-yl)-6-methyl-8α-ergolinyl]-1,1-diethylurea (12% yield).

후처리

  1. temperatureis cooled in an ice bath
  2. extractionextracted with methylene chloride
  3. washThe organic phases are washed with water
  4. dry with materialdried over magnesium sulfate
  5. customThe concentrated residue is chromatographed under pressure on silica gel with ethyl acetate/methanol 95:5

출처 및 근거

ORD 기록
ord-0bd8e2a6c5414cce8d6f8ddc70fc0fb6
출처 데이터셋
uspto-grants-1989_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04847262

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