Trifluoroacetic acid → HCID 10594394, compound

HRID 356987Notes

Reaction equation

HRID 356987 reaction equation
[Cl:1][C:2]1[N:6]([C@@H:7]2[O:31][C@H:30](COC(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[C@@H:9]([O:10]C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[C@@H]2F)[C:5]2[CH:54]=[C:55]([Cl:59])[C:56]([Cl:58])=[CH:57][C:4]=2[N:3]=1.[C:60]([OH:66])([C:62](F)(F)[F:63])=O>C(Cl)(Cl)Cl>[Cl:1][C:2]1[N:6]([C@@H:7]2[O:31][C@H:30]([CH2:9][OH:10])[C@H:62]([F:63])[C@H:60]2[OH:66])[C:5]2[CH:54]=[C:55]([Cl:59])[C:56]([Cl:58])=[CH:57][C:4]=2[N:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 10676977HCID 10676977, compound

Product 1

HCID 10594394HCID 10594394, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

While the desired 3',5'-di-O-trityl derivative, compound 2, was only obtained in 10% yield from compound 1, the isomeric 2',5'-ditrityl derivative, compound 3, was obtained in a 30% yield. The fluorination of compound 3 using DAST and pyridine in CH2Cl2 gave 2,5,6-trichloro-1-(2,5-di-O-trityl-3-deoxy-3-fluoro-β-D-xylofuranosyl)benzimidazole (compound 5) in a 71% yield. The fluorination of compound 2 using the same conditions gave 2,5,6-trichloro-1-(3,5-di-O-trityl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)benzimidazole (compound 4) in a 63% yield. Both compounds 4 and 5 were deprotected using 10% CF3COOH in CHCl3 to give good yields of the deprotected nucleosides 2,5,6-trichloro-1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)benzimidazole (compound 6) and 2,5,6-trichloro-1-(3-deoxy-3-fluoro-β-D-xylofuranosyl)benzimidazole (compound 7), respectively.

Workup

  1. customto give good

Sources & evidence

ORD record
ord-c8d2a83619154d4599950bc777076264
Source dataset
uspto-grants-1998_11
Patent number
US05840743

Reaction notes

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