Reaktion #2334

Reaktionsgleichung

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

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe DMF was evaporated in vacuo
2. 2
   Sonstigethe residue partitioned between dichloromethane and water
3. 3
   ExtraktionThe aqueous phase was extracted with further dichloromethane
4. 4
   WaschenThe combined organic extracts were washed with water
5. 5
   Sonstigethen dried
6. 6
   Sonstigeevaporated
7. 7
   SonstigeThe residue was purified by chromatography on alumina
8. 8
   Wascheneluting with dichloromethane
9. 9
   SonstigeEvaporation of the appropriate fractions

Vorschrift

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)+.

Quelle