Réaction #2334

Équation de réaction

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

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   AutreThe DMF was evaporated in vacuo
2. 2
   Autrethe residue partitioned between dichloromethane and water
3. 3
   ExtractionThe aqueous phase was extracted with further dichloromethane
4. 4
   LavageThe combined organic extracts were washed with water
5. 5
   Autrethen dried
6. 6
   Autreevaporated
7. 7
   AutreThe residue was purified by chromatography on alumina
8. 8
   Lavageeluting with dichloromethane
9. 9
   AutreEvaporation of the appropriate fractions

Mode opératoire

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)+.

Source