Ammonia → Terguride

HRID 231703노트

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HRID 231703 반응식
C(OC([C:11]1[NH:25][C:24]2[C:26]3[C:12]=1[CH2:13][C@@H:14]1[C@@H:19]([C:20]=3[CH:21]=[CH:22][CH:23]=2)[CH2:18][C@H:17]([NH:27][C:28]([N:30]([CH2:33][CH3:34])[CH2:31][CH3:32])=[O:29])[CH2:16][N:15]1[CH3:35])=O)C1C=CC=CC=1.N>C(O)CO>[CH2:33]([N:30]([CH2:31][CH3:32])[C:28](=[O:29])[NH:27][C@H:17]1[CH2:18][C@H:19]2[C@@H:14]([CH2:13][C:12]3[C:26]4[C:24](=[CH:23][CH:22]=[CH:21][C:20]2=4)[NH:25][CH:11]=3)[N:15]([CH3:35])[CH2:16]1)[CH3:34]

참가 물질

4

반응물 2

HCID 222AmmoniaHCID 135590328alpha-(3,3-Diethylureido)-6-methylergoline-2-carboxylic acid benzyl ester

생성물 1

HCID 443951Terguride수율 85.3%

시약·촉매·용매 1

HCID 174Ethylene Glycol용매

실험 절차

150 mg (0.31 mmol) of 8α-(3,3-diethylureido)-6-methylergoline-2-carboxylic acid benzyl ester is heated in 3 ml of a saturated solution of ammonia in ethylene glycol for 3 hours to 100° C. After dilution with water, the mixture is extracted with ethyl acetate and the organic phase washed with saturated sodium chloride solution, dried over magnesium sulfate, filtered, and concentrated. The residue is chromatographed over silica gel with methylene chloride/ethanol=8:1. After trituration in ethanol/hexane/ether, 90 mg of 8α-(3,3-diethylureido)-6-methylergoline)-2-carboxylic acid amide is obtained, mp 171°-173° C.

후처리

  1. extractionAfter dilution with water, the mixture is extracted with ethyl acetate
  2. washthe organic phase washed with saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is chromatographed over silica gel with methylene chloride/ethanol=8:1

출처 및 근거

ORD 기록
ord-5ae42176cf7842f7b288a3e270eab8ce
출처 데이터셋
uspto-grants-1989_07
특허 번호
US04847262

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