反应详情

A solution of 2-{[5-amino-1-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-4-(4-methylphenyl)-1H-pyrazol-3-yl]oxy}ethyl acetate (0.35 g) (Preparation 30), 4-(tert-butyl)phenylsulfonyl chloride (0.25 g) and 4-(N,N-dimethyl)aminopyridine (98 mg) in pyridine (4 ml) was stirred at room temperature overnight. Tlc (30:70 ethyl acetate/hexane) indicated a new less polar product had formed, but the reaction appeared to have proceeded only 50% to completion. A further aliquot of the sulfonyl chloride (0.25 g) was added to the reaction mixture and stirring at room temperature was continued for a further 4 days. Tic analysis then indicated complete disappearance of the starting materials and a single new product was observed. The reaction mixture was poured into saturated copper (II) sulfate solution (100 ml) and the aqueous mixture was extracted with ether (2×50 ml). The combined ether extracts were washed with saturated copper (II) sulfate solution (30 ml). The organic extract was dried over magnesium sulfate, filtered and concentrated under reduced pressure to leave a yellow/brown gum. The gum was recrystallised from methanol/water to give the title compound as yellow crystals (325 mg).

1. customhad formed
2. extractionthe aqueous mixture was extracted with ether (2×50 ml)
3. washThe combined ether extracts were washed with saturated copper (II) sulfate solution (30 ml)
4. extractionThe organic extract
5. dry with materialwas dried over magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customto leave a yellow/brown gum
9. customThe gum was recrystallised from methanol/water