Sodium hydride → 2,5,6-Trichloro-1-(2,3,5-tri-O-benzyl-beta-D-arabinofuranosyl)benzimidazole

HRID 263890

반응식

HRID 263890 반응식
[Cl:1][C:2]1[NH:3][C:4]2[CH:10]=[C:9]([Cl:11])[C:8]([Cl:12])=[CH:7][C:5]=2[N:6]=1.[H-].[Na+].[CH2:15]([O:22][C@H:23]1[C@H:27]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C@@H:26]([CH2:36][O:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[O:25][CH:24]1Cl)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CC#N>[Cl:1][C:2]1[N:3]([C@@H:24]2[O:25][C@H:26]([CH2:36][O:37][CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[C@@H:27]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C@@H:23]2[O:22][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:4]2[CH:10]=[C:9]([Cl:11])[C:8]([Cl:12])=[CH:7][C:5]=2[N:6]=1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 2860092,5,6-Trichloro-1H-benzimidazoleHCID 127994081-chloro-Tri-2,3,5-O-benzyl-D-arabofuranose

생성물 1

HCID 539929402,5,6-Trichloro-1-(2,3,5-tri-O-benzyl-beta-D-arabinofuranosyl)benzimidazole수율 95%

시약·촉매·용매 1

HCID 6342Acetonitrile용매2회

실험 절차

Compound 5 (598 mg 2.7 mmole) was dissolved in dry CH3CN(60 ml) and 97% NaH (80 mg, 3 mmole) was added. The mixture was stirred under N2 for 1 hour at room temperature. Then 2,3,5-tri-O-benzyl-D-arabinofuranosyl chloride (prepared from 2,3,5-tri-O-benzyl-1-O-p-nitrobenzoyl-D-arabinofuranose) (1.83 g, 3 mmole)) dissolved in dry CH3CN (20 ml) was added dropwise. The mixture was stirred under N2 for overnight at room temperature. The reaction solution was filtered through Celite. The filtrate was evaporated to give a syrup and this syrup was subjected to flash column chromatography on silica gel (Kieselgel 60, 230-400 mesh) and eluted with CH2Cl2. The fractions containing 133 were combined and evaporated to give 1.6 g (95.0%) of 133. (IR KBr cm-1 : 1140-1060 (C--O--C)).

후처리

  1. additionwas added dropwise
  2. stirringThe mixture was stirred under N2 for overnight at room temperature
  3. filtrationThe reaction solution was filtered through Celite
  4. customThe filtrate was evaporated
  5. customto give a syrup
  6. washeluted with CH2Cl2
  7. additionThe fractions containing 133
  8. customevaporated

출처 및 근거

ORD 기록
ord-ae85ec8d6d95409c851a5eb9f748bfd7
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05646125

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