Hydrochloric Acid → Ammonia

Di-tert-butyl{9-[4-({3-[(R)-cyclohexyl(hydroxy)phenylmethyl]-1H-1,2,4-triazol-1-yl}methyl)piperdin-1-yl]nonyl}imidodicarbonate (Preparation 5, 2.6 g, 3.7 mmol) was dissolved in dichloromethane (15 ml) and hydrogen chloride in diethylether (2M, 15 ml, 30 mmol) added. After stirring at room temperature for 5 hours the solvent was removed in vacuo, the residue was partitioned between dichloromethane (200 ml) and saturated aqueous sodium bicarbonate solution (200 ml). The organic layer was separated, dried over magnesium sulphate, filtered and the solvent removed in vacuo. The residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:880 ammonia (97.5:2.5:0.25, by volume) to furnish the title compound as a clear oil, in 70% yield, 1.29 g (contains 10% of other triazole regio-isomer).

1. customwas removed in vacuo
2. customthe residue was partitioned between dichloromethane (200 ml) and saturated aqueous sodium bicarbonate solution (200 ml)
3. customThe organic layer was separated
4. dry with materialdried over magnesium sulphate
5. filtrationfiltered
6. customthe solvent removed in vacuo
7. customThe residue was purified by column chromatography on silica gel eluting with dichloromethane

ORD-Eintrag

ord-38e3ba30746a47c5b598f07b623da761

Quelldatensatz

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08263623B2