Ethoxyquin → HCID 54439761, 화합물

HRID 1659856

반응식

HRID 1659856 반응식
[C:1]([NH:4][C@@:5]1(O)[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][CH:6]1Cl)(=[O:3])[CH3:2].[CH3:26][CH2:27][O:28][C:29]1[CH:34]=[C:33]2[C:35]([CH3:41])=[CH:36][C:37]([CH3:40])([CH3:39])[NH:38][C:32]2=[CH:31][CH:30]=1>CC(C)=O>[C:1]([NH:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][CH:6]1[N:38]1[C:32]2[C:33](=[CH:34][C:29]([O:28][CH2:27][CH3:26])=[CH:30][CH:31]=2)[C:35]([CH3:41])=[CH:36][C:37]1([CH3:39])[CH3:40])(=[O:3])[CH3:2]

참가 물질

4

반응물 2

HCID 3293EthoxyquinHCID 54014248HCID 54014248, 화합물

생성물 1

HCID 54439761HCID 54439761, 화합물수율 63%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

2-Acetamido-3,4,6-tri-O-acetyl-D-glucopyranosyl chloride (18.3 g) and ethoxyquin (22.1 g) were vigorously stirred together at 80° for 3 hours. Acetone (50 ml) was added to the hot reaction mixture and stirring was continued for 0.5 hours. After cooling, the solid ethoxyquin-hydrochloride was filtered, washed with acetone and the combined filtrates were evaporated under reduced pressure. The crude product was purified by column chromatography on silica (ethylacetate-benzene 1:4). 16.5 g of 1-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-D-glucopyranosyl)-6-ethoxy-1,2-dihydro-2,2,4-trimethylquinoline were obtained. Analytical grade sample was obtained by recrystallisation from ether or isopropanol. m.p. 186°-187°.

후처리

  1. temperatureAfter cooling
  2. filtrationthe solid ethoxyquin-hydrochloride was filtered
  3. washwashed with acetone
  4. customthe combined filtrates were evaporated under reduced pressure
  5. customThe crude product was purified by column chromatography on silica (ethylacetate-benzene 1:4)

출처 및 근거

ORD 기록
ord-2627c3d3ed04474daa7d8ab0bd7d06b5
출처 데이터셋
uspto-grants-1981_12
특허 번호
US04305932

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