Reacción #820085

ord-391687f79290480c858a3cea658ed0d2

Ecuación de reacción

C#CCC1CCN(C(=O)Oc2ccc(F)cc2)CC1
4-fluorophenyl 4-(prop-2-ynyl)piperidine-1-carboxylate
Nc1nc(I)nc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O
2-iodoadenosine
→
Nc1nc(C#CCC2CCN(C(=O)Oc3ccc(F)cc3)CC2)nc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O
2-{3-[1-((4-Fluorophenoxy)carbonyl)piperidin-4-yl]propyn-1-yl}adenosine

Reactantes

C#CCC1CCN(C(=O)Oc2ccc(F)cc2)CC1
4-fluorophenyl 4-(prop-2-ynyl)piperidine-1-carboxylate
Nc1nc(I)nc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O
2-iodoadenosine

Reactivos

Ninguno

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroHPLC rt=7.6 min.

Procedimiento

Batch: AB-9-147. 4-fluorophenyl 4-(prop-2-ynyl)piperidine-1-carboxylate, batch JR28-97 (0.700 g, 2.68 mmol) was added to a solution of 2-iodoadenosine (0.812 g, 2.065 mmol) according to general procedure 2. Yield: 0.902 g, 83%. 1H NMR (CD3OD) δ 8.34 (s, 1H), 7.11 (m, 4H), 5.98 (d, 1H), 4.76 (m, 2H), 4.37-4.19 (2×m, 3H), 3.95-3.75 (2×d, 2H), 3.07-2.93 (2×bt, 4H), 2.47 (d, 5H), 1.98-1.44 (2×m, SH). m/z MH+=527.19. HPLC rt=7.6 min.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07589076B2uspto-grants-2009_09