Citric Acid → HCID 21967943, 화합물

HRID 1003936노트

반응식

HRID 1003936 반응식
[O:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[C:7]([CH2:10][CH2:11][C:12]([C:14]3[C:19]([O:20][CH2:21][CH:22]=[CH2:23])=[CH:18][C:17]([CH3:24])=[CH:16][C:15]=3[O:25][C@@H:26]3[O:34][C@H:33]([CH2:35][OH:36])[C@@H:31]([OH:32])[C@H:29]([OH:30])[C@H:27]3[OH:28])=[O:13])[CH:8]=[CH:9][C:2]1=2.C(=O)=O.CC(C)=O.Cl[C:45]([O:47][CH3:48])=[O:46].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>N1C(C)=CC(C)=CC=1C.ClCCl>[O:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[C:7]([CH2:10][CH2:11][C:12]([C:14]3[C:19]([O:20][CH2:21][CH:22]=[CH2:23])=[CH:18][C:17]([CH3:24])=[CH:16][C:15]=3[O:25][C@@H:26]3[O:34][C@H:33]([CH2:35][O:36][C:45]([O:47][CH3:48])=[O:46])[C@@H:31]([OH:32])[C@H:29]([OH:30])[C@H:27]3[OH:28])=[O:13])[CH:8]=[CH:9][C:2]1=2

참가 물질

7

반응물 4

HCID 311Citric AcidHCID 6586Methyl chloroformateHCID 10601391HCID 10601391, 화합물HCID 18522661Acetone cardice

생성물 1

HCID 21967943HCID 21967943, 화합물수율 87.2%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 79532,4,6-Trimethylpyridine용매

실험 절차

3-(5-Benzo[b]furanyl)-2'-(β-D-glucopyranosyloxy)-6'-allyloxy-4'-methylpropiophenone (500 mg) is dissolved in 2,4,6-collidine (5 ml), and the mixture is cooled to 40° C. with dry ice-acetone, and thereto is added dropwise a solution of methyl chloroformate (114 mg) in dichloromethane (0.5 ml) with stirring. The mixture is stirred at 40° C. for one hour, and stirred at room temperature for 1.5 hour. The reaction mixture is poured into cold 10% aqueous citric acid solution, and the mixture is extracted with ethyl acetate. The organic layer is washed with water, dried, and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (solvent; chloroform/methanol) to give 3-(5-benzo[b]furanyl)-2'-(6-O-methoxycarbonyl-β-D-glucopyranosyloxy)-6'-allyloxy-4'-methylpropiophenone (487 mg).

후처리

  1. stirringThe mixture is stirred at 40° C. for one hour
  2. stirringstirred at room temperature for 1.5 hour
  3. extractionthe mixture is extracted with ethyl acetate
  4. washThe organic layer is washed with water
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue is purified by silica gel column chromatography (solvent; chloroform/methanol)

출처 및 근거

ORD 기록
ord-2e55ee8970be49a6a8b07a7ae20e825a
출처 데이터셋
uspto-grants-2000_04
특허 번호
US06048842

반응 노트

불러오는 중…