Reacción #44902

ord-f51fbbafbca743e880e1d200adcdec08

Ecuación de reacción

C[O-].[Na+]
sodium methoxide
CCn1nnc([C@H]2O[C@@H](n3cnc4c(N[C@H]5CC[C@H](Nc6nc(NCCc7cn(C)cn7)nc7c6ncn7[C@@H]6O[C@H](c7nnn(CC)n7)[C@@H](OC(C)=O)[C@H]6OC(C)=O)CC5)nc(NCCc5cn(C)cn5)nc43)[C@H](OC(C)=O)[C@@H]2OC(C)=O)n1
solution
CCn1nnc([C@H]2O[C@@H](n3cnc4c(N[C@H]5CC[C@H](Nc6nc(NCCc7cn(C)cn7)nc7c6ncn7[C@@H]6O[C@H](c7nnn(CC)n7)[C@@H](OC(C)=O)[C@H]6OC(C)=O)CC5)nc(NCCc5cn(C)cn5)nc43)[C@H](OC(C)=O)[C@@H]2OC(C)=O)n1
Trans-1,4-cyclohexanediylbis[imino(2-{[2-(1-methyl-1H-imidazol-4-yl)ethyl]amino}-9H-purine-6,9-diyl)(2R,3R,4R,5R)-5-(2-ethyl-2H-tetrazol-5-yl)tetrahydrofuran-2,3,4-triyl] tetraacetate
C[O-].[Na+]
sodium methoxide
→
CCn1nnc([C@H]2O[C@@H](n3cnc4c(N[C@H]5CC[C@H](Nc6nc(NCCc7cn(C)cn7)nc7c6ncn7[C@@H]6O[C@H](c7nnn(CC)n7)[C@@H](O)[C@H]6O)CC5)nc(NCCc5cn(C)cn5)nc43)[C@H](O)[C@@H]2O)n1
title Compound
Rendimiento 97.8%
CCn1nnc([C@H]2O[C@@H](n3cnc4c(N[C@H]5CC[C@H](Nc6nc(NCCc7cn(C)cn7)nc7c6ncn7[C@@H]6O[C@H](c7nnn(CC)n7)[C@@H](O)[C@H]6O)CC5)nc(NCCc5cn(C)cn5)nc43)[C@H](O)[C@@H]2O)n1
(2R,3R,4S,5R,2′R,3′R,4′S,5′R)-2,2′-{trans-1,4-cyclohexanediylbis[imino(2-{[2-(1-methyl-1H-imidazol-4-yl)ethyl]amino}-9H-purine-6,9-diyl)]}bis[5-(2-ethyl-2H-tetrazol-5-yl)tetrahydro-3,4-furandiol]
Rendimiento 97.8%

Reactantes

C[O-].[Na+]
sodium methoxide
CCn1nnc([C@H]2O[C@@H](n3cnc4c(N[C@H]5CC[C@H](Nc6nc(NCCc7cn(C)cn7)nc7c6ncn7[C@@H]6O[C@H](c7nnn(CC)n7)[C@@H](OC(C)=O)[C@H]6OC(C)=O)CC5)nc(NCCc5cn(C)cn5)nc43)[C@H](OC(C)=O)[C@@H]2OC(C)=O)n1
solution
CCn1nnc([C@H]2O[C@@H](n3cnc4c(N[C@H]5CC[C@H](Nc6nc(NCCc7cn(C)cn7)nc7c6ncn7[C@@H]6O[C@H](c7nnn(CC)n7)[C@@H](OC(C)=O)[C@H]6OC(C)=O)CC5)nc(NCCc5cn(C)cn5)nc43)[C@H](OC(C)=O)[C@@H]2OC(C)=O)n1
Trans-1,4-cyclohexanediylbis[imino(2-{[2-(1-methyl-1H-imidazol-4-yl)ethyl]amino}-9H-purine-6,9-diyl)(2R,3R,4R,5R)-5-(2-ethyl-2H-tetrazol-5-yl)tetrahydrofuran-2,3,4-triyl] tetraacetate
C[O-].[Na+]
sodium methoxide

Reactivos

Ninguno

Disolventes

CO
methanol

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    workup.ADDITIONAfter 30 minutes Dowex 50 [H+] was added
  2. 2
    FiltraciónThe resin was filtered off
  3. 3
    Otrothe filtrate was evaporated

Procedimiento

A solution of Stage 3 (28.6 g; assume 24.7 mmol) in methanol (515 ml) was treated with sodium methoxide (0.44 g, 8.13 mmol) for 90 minutes before being treated with a further portion of sodium methoxide (0.44 g, 8.13 mmol). After 30 minutes Dowex 50 [H+] was added to neutralise the solution. The resin was filtered off and the filtrate was evaporated to leave the title Compound as a foam (24 g).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07737126B2uspto-grants-2010_06