Reacción #2334

Ecuación de reacción

Sodium hydride

product

4-[N-(4-pyridyl)-N-tertiary-butyloxycarbonylamino]phenol

ethyl 6-bromohexanoate

→

ethyl 6-[4-[N-(4-pyridyl)-N-tertiary-butyloxycarbonylamino]phenoxy]hexanoate

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe DMF was evaporated in vacuo
2. 2
   Otrothe residue partitioned between dichloromethane and water
3. 3
   ExtracciónThe aqueous phase was extracted with further dichloromethane
4. 4
   LavadoThe combined organic extracts were washed with water
5. 5
   Otrothen dried
6. 6
   Otroevaporated
7. 7
   OtroThe residue was purified by chromatography on alumina
8. 8
   Lavadoeluting with dichloromethane
9. 9
   OtroEvaporation of the appropriate fractions

Procedimiento

Sodium hydride (50% w/w dispersion in mineral oil, 55 mg) was added under argon to a stirred solution of the product from step (iii) above (300 mg) in dry DMF (5 ml). After five minutes, ethyl 6-bromohexanoate (0.20 ml) was added and the mixture stirred for 16 hours. The DMF was evaporated in vacuo and the residue partitioned between dichloromethane and water. The aqueous phase was extracted with further dichloromethane. The combined organic extracts were washed with water then dried, and evaporated. The residue was purified by chromatography on alumina, eluting with dichloromethane and then 1% v/v methanol/dichloromethane. Evaporation of the appropriate fractions gave ethyl 6-[4-[N-(4-pyridyl)-N-tertiary-butyloxycarbonylamino]phenoxy]hexanoate, 260 mg, as a yellow gum: NMR (CDCl3) δ 8.40 (2H, dd), 7.16 (2H, dd), 7.07 (2H, m), 6.90 (2H, m), 4.13 (2H, q), 3.98 (2H, t), 2.34 (2H, t), 1.78 (4H, m), 1.57 (2H, m), 1.44 (9H, s), 1.26 (3H, t); m/e 429 (M+H)+.

Fuente