Sodium hydride → 3-(6-Methylergolin-8beta-ylmethyl)oxazolidin-2-one

HRID 986524노트

반응식

HRID 986524 반응식
[H-].[Na+].[O:3]1[CH2:7][CH2:6][NH:5][C:4]1=[O:8].S(C1C=CC(C)=CC=1)(O[CH2:13][C@@H:14]1[CH2:28][C@H:27]2[C@@H:17]([CH2:18][C:19]3[C:29]4[C:22](=[CH:23][CH:24]=[CH:25][C:26]2=4)[NH:21][CH:20]=3)[N:16]([CH3:30])[CH2:15]1)(=O)=O>CN(C)C=O>[CH3:30][N:16]1[C@H:17]2[C@@H:27]([C:26]3[CH:25]=[CH:24][CH:23]=[C:22]4[C:29]=3[C:19]([CH2:18]2)=[CH:20][NH:21]4)[CH2:28][C@@H:14]([CH2:13][N:5]2[CH2:6][CH2:7][O:3][C:4]2=[O:8])[CH2:15]1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 739492-OxazolidinoneHCID 139330156-Methylergolin-8beta-ylmethyl tosylate

생성물 1

HCID 103816823-(6-Methylergolin-8beta-ylmethyl)oxazolidin-2-one수율 82%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

0.5 g of 50% sodium hydride in an oil was added in small portions to a mixture of 2.0 g of oxazolidin-2-one and 15 ml of dimethylformamide, and the resulting mixture was stirred for 30 minutes. 2.0 g of 6-methylergolin-8β-ylmethyl tosylate was added to the mixture which was then heated on a water bath for 1 hour. The solvent was distilled off under reduced pressure, and the residue (which was dissolved in dichloromethane and adsorbed on silica gel) was purified by silica gel column chromatography (eluted with ethyl acetate:isopropyl alcohol=1:1 by volume). The product was recrystallized from isopropyl alcohol to obtain 1.3 g of the titled compound as colorless needles having a melting point higher than 240° C. (with decomposition).

후처리

  1. temperaturewas then heated on a water bath for 1 hour
  2. distillationThe solvent was distilled off under reduced pressure
  3. dissolutionthe residue (which was dissolved in dichloromethane and adsorbed on silica gel)
  4. customwas purified by silica gel column chromatography (eluted with ethyl acetate:isopropyl alcohol=1:1 by volume)
  5. customThe product was recrystallized from isopropyl alcohol

출처 및 근거

ORD 기록
ord-276f94bc1eb249d1bad7c1877b5ab976
출처 데이터셋
uspto-grants-1987_12
특허 번호
US04713457

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