Reacción #820091

ord-babd4fc937b14748abe8dac41ae8219a

Ecuación de reacción

C#CCC1CCN(C(=O)OCc2ccc([N+](=O)[O-])cc2)CC1
4-nitrobenzyl 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)OCc3ccc([N+](=O)[O-])cc3)CC2)nc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O
2-{3-[1-((4-Nitro)benzyloxycarbanoyl)piperidin-4-yl]propyn-1-yl}adenosine

Reactantes

—
JR28-109
C#CCC1CCN(C(=O)OCc2ccc([N+](=O)[O-])cc2)CC1
4-nitrobenzyl 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=5.8 min.

Procedimiento

Batch: AB-10-021. 4-nitrobenzyl 4-(prop-2-ynyl)piperidine-1-carboxylate, batch JR28-109 (0.743 g, 2.458 mmol) was added to a solution of 2-iodoadenosine (0.658 g, 1.674 mmol) according to general procedure 2. Yield: 0.694 g, 42%. 1H NMR (CD3OD) δ 8.29 (s, 1H), 8.18-7.56 (2×d, 4H), 5.94 (d, 1H), 5.23 (s, 2H), 4.69 (m, 2H), 4.31-4.14 (2×m, 3H), 3.84-3.74 (2×d, 2H), 3.10-2.90 (bs, 4H), 2.44 (d, 5H), 1.91-1.40 (2×m, 5H). m/z MH+=568.10. HPLC rt=5.8 min.

Fuente

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