Isoindoline → 1-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)-4-chloro-3-(1,3-dihydro-isoindol-2-ylmethyl)benzene

HRID 1625752노트

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HRID 1625752 반응식
[C:1]([O: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][C@H:6]1[C:24]1[CH:25]=[CH:26][C:27]([Cl:32])=[C:28]([CH:31]=1)[CH:29]=O)(=[O:3])[CH3:2].[CH2:33]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH2:35][NH:34]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>ClCCCl.C(O)(=O)C>[C:1]([O: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][C@H:6]1[C:24]1[CH:25]=[CH:26][C:27]([Cl:32])=[C:28]([CH2:29][N:34]2[CH2:35][C:36]3[C:41](=[CH:40][CH:39]=[CH:38][CH:37]=3)[CH2:33]2)[CH:31]=1)(=[O:3])[CH3:2]

참가 물질

7

반응물 4

HCID 422478IsoindolineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 601358015-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)-2-chloro benzaldehyde

생성물 1

HCID 666086231-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)-4-chloro-3-(1,3-dihydro-isoindol-2-ylmethyl)benzene수율 59.1%

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 176Acetic Acid용매

실험 절차

To a mixed solution of the above 5-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2-chlorobenzaldehyde 83 (325 mg), 2,3-dihydro-1H-isoindole (98 mg), acetic acid (82 mg) in 1,2-dichloroethane (5 ml) was added sodium triacetoxyborohydride (219 mg). The mixture was stirred at room temperature for 3 hours, and cooled to 0° C. A saturated aqueous sodium hydrogen carbonate solution was added thereto to basify the reaction mixture. The mixture was extracted with ethyl acetate, and the extract was washed with brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:0-1:1) to give 1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-4-chloro-3-(1,3-dihydro-isoindol-2-ylmethyl)benzene 84 (234 mg) as a colorless solid. APCI-Mass m/Z 574/576 (M+H).

후처리

  1. temperaturecooled to 0° C
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe extract was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:0-1:1)

출처 및 근거

ORD 기록
ord-91e81021ed8b4f77ad77ac93d445cc15
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785403B2

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