Reacción #583489

ord-7294be9dc7a1496da96bccbb1c3cfef8

Ecuación de reacción

O=C([O-])O.[Na+]
NaHCO3
CC(C)[C@]12O[C@H]1[C@@H]1O[C@]13[C@]1(O[C@H]1C[C@H]1C4=C(CC[C@@]13C)C(=O)OC4)[C@@H]2O
PG490
CCN(CC)S(F)(F)F
(diethylamino)sulfur trifluoride
→
CC(C)[C@]12O[C@H]1[C@@H]1O[C@]13[C@]1(O[C@H]1C[C@H]1C4=C(CC[C@@]13C)C(=O)OC4)[C@H]2F
desired product
CC(C)[C@]12O[C@H]1[C@@H]1O[C@]13[C@]1(O[C@H]1C[C@H]1C4=C(CC[C@@]13C)C(=O)OC4)[C@H]2F
14-deoxy-14α-fluoro triptolide

Reactantes

O=C([O-])O.[Na+]
NaHCO3
CC(C)[C@]12O[C@H]1[C@@H]1O[C@]13[C@]1(O[C@H]1C[C@H]1C4=C(CC[C@@]13C)C(=O)OC4)[C@@H]2O
PG490
CCN(CC)S(F)(F)F
(diethylamino)sulfur trifluoride

Reactivos

Ninguno

Disolventes

ClCCl
dichloromethane

Condiciones de reacción

Temperatura
0°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    ExtracciónThe reaction mixture was extracted with 3×2 ml of dichloromethane
  2. 2
    SecadoThe combined organic layer was dried over anhydrous NaSO4
  3. 3
    Concentraciónconcentrated under vacuum

Procedimiento

To a solution of PG490 (triptolide, 17.3 mg, 0.048 mmol) in dichloromethane (1.0 ml) at 0° C. was added (diethylamino)sulfur trifluoride (DAST, 100 μl, 0.763 mmol) under N2. The reaction mixture was stirred at 0° C. for 2 hrs, and saturated NaHCO3 solution (0.8 ml) was then added. The reaction mixture was extracted with 3×2 ml of dichloromethane. The combined organic layer was dried over anhydrous NaSO4 and concentrated under vacuum. The desired product (PG763) was obtained in quantitative yield.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US06943259B2uspto-grants-2005_09