Reacción #1350603

Ecuación de reacción

THF

tert-butyl (3S)-3-amino-2-oxoperhydroazepine-1-acetate

sodium carbonate

THF

→

tert-butyl (3S)-3-(9-fluorenylmethoxycarbonylamino)-2-oxoperhydroazepine-1-acetate

Disolventes

Water

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónthe reaction mixture extracted with ethyl acetate (3×100 ml)
2. 2
   LavadoThe combined extracts were washed with brine (100 ml)
3. 3
   Secadodried (MgSO4)
4. 4
   Otroevaporated
5. 5
   OtroThe residue was purified by MPLC on silica
6. 6
   Lavadoeluting initially with dichloromethane
7. 7
   Temperaturagradually increasing to 15% ethyl acetate/dichloromethane

Procedimiento

A solution of tert-butyl (3S)-3-amino-2-oxoperhydroazepine-1-acetate (7 g) in THF (50 me) was added to a solution of sodium carbonate (3 g) in water (30 ml). A solution of N-(9-fluorenylmethoxycarbonyloxy)succimimide (9.7 g) in THF (100 ml) was then added dropwise over 30 minutes with stirring. The reaction mixture was stired at ambient temperature for a further 30 minutes. Water (200 ml) was added and the reaction mixture extracted with ethyl acetate (3×100 ml). The combined extracts were washed with brine (100 ml), dried (MgSO4) and evaporated. The residue was purified by MPLC on silica, eluting initially with dichloromethane and gradually increasing to 15% ethyl acetate/dichloromethane to give tert-butyl (3S)-3-(9-fluorenylmethoxycarbonylamino)-2-oxoperhydroazepine-1-acetate (10.9 g) as a clear oil; NMR (d6-DMSO): 1.45 (s, 9H), 1.5-2.15 (m, 6H), 3.1-3.25 (m, 1H), 3.6-3.75 (m, 1H), 4.0-4.5 (m, 5H), 6.25 (d, 1H), 7.25-7.45 (m, 4H), 7.6 (d, 2H), 7.75 (d, 2H); mass spectroscopy, m/e (ES+) 465.2 (MH+).

Fuente