Reacción #820086

ord-3dbfef74a8454c3194f1bfb421c4be68

Ecuación de reacción

C#CCC1CCN(C(=O)Oc2ccc([N+](=O)[O-])cc2)CC1
4-nitrophenyl 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([N+](=O)[O-])cc3)CC2)nc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O
2-{3-[1-((4-Nitrophenoxy)carbonyl)piperidin-4-yl]propyn-1-yl}adenosine

Reactantes

C#CCC1CCN(C(=O)Oc2ccc([N+](=O)[O-])cc2)CC1
4-nitrophenyl 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=7.3 mm

Procedimiento

Batch: AB-9-149. 4-nitrophenyl 4-(prop-2-ynyl)piperidine-1-carboxylate, batch JR28-97 (0.630 g, 2.185 mmol) was added to a solution of 2-iodoadenosine (0.727 g, 1.849 mmol) according to general procedure 2. Yield: 1.192 g, 65%. %. 1H NMR (CD3OD) δ 8.26 (m, 1H), 8.25-7.34 (2×m, 4H), 5.94 (d, 1H), 4.72 (m, 2H), 4.32-4.14 (2×m, 3H), 3.91-3.71 (2×d, 2H), 3.17-2.90 (2×bt, 4H), 2.48 (d, 5H), 1.45 (m, 5H). m/z MH+=554.15. HPLC rt=7.3 mm.

Fuente

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