Methanol → 2,5,6-Trichloro-1-(beta-D-arabinofuranosyl)benzimidazole

HRID 1900125Notes

Reaction equation

HRID 1900125 reaction equation
[Cl:1][C:2]1[N:6]([C@@H:7]2[O:27][C@H:26]([CH2:28][O:29]CC3C=CC=CC=3)[C@@H:17]([O:18]CC3C=CC=CC=3)[C@@H:8]2[O:9]CC2C=CC=CC=2)[C:5]2[CH:37]=[C:38]([Cl:42])[C:39]([Cl:41])=[CH:40][C:4]=2[N:3]=1.B(Cl)(Cl)Cl.CO.[NH4+].[OH-]>C(Cl)Cl>[Cl:1][C:2]1[N:6]([C@@H:7]2[O:27][C@H:26]([CH2:28][OH:29])[C@@H:17]([OH:18])[C@@H:8]2[OH:9])[C:5]2[CH:37]=[C:38]([Cl:42])[C:39]([Cl:41])=[CH:40][C:4]=2[N:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 14923Ammonium HydroxideHCID 25135Boron TrichlorideHCID 539929402,5,6-Trichloro-1-(2,3,5-tri-O-benzyl-beta-D-arabinofuranosyl)benzimidazole

Product 1

HCID 536983582,5,6-Trichloro-1-(beta-D-arabinofuranosyl)benzimidazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Compound 133 (1.25 g 2 mmole) was dissolved in dry CH2Cl2 (20 ml) and this solution was cooled in an acetone-dry ice bath. A 1M solution of BCl3 in CH2Cl2 (10 ml) was added and the mixture was stirred at -70° for 4.5 hr. At this point TLC showed no starting material. CH3OH (10 ml) was added and the solution was made neutral with NH4OH. The solution was evaporated in vacuo to dryness. H2O (20 ml) was added and the solution was extracted with EtOAc. The EtOAc layer was washed with H2O, dried (Na2SO4) and evaporated in vacuo to obtain a syrup. This syrup was subjected to flash column chromatography on silica gel (Kieselgel 60, 230-400 mesh) with CH2Cl -MeOH (20:1) as eluent solvent to give 134. Yield 0.551 g, 77.9%.

Workup

  1. temperaturethis solution was cooled in an acetone-dry ice bath
  2. customThe solution was evaporated in vacuo to dryness
  3. additionH2O (20 ml) was added
  4. extractionthe solution was extracted with EtOAc
  5. washThe EtOAc layer was washed with H2O
  6. dry with materialdried (Na2SO4)
  7. customevaporated in vacuo
  8. customto obtain a syrup

Sources & evidence

ORD record
ord-95365ddb34904a929765aae39cb81ca8
Source dataset
uspto-grants-1996_11
Patent number
US05574058

Reaction notes

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