反应详情

A mixture of (E)-(2-(2-(2-(4-(1-(3-(6-bromopyridin-2-yl)-2-cyanoacrylamido)butyl)phenoxy)ethoxy)ethoxy)ethyl)imidodicarbonic acid, 1,3-bis-tert-butyl ester (47; 105 mg, 0.14 mmol) and trifluoroacetic acid (0.3 mL) was stirred in dichloromethane (3 mL) for 1.5 hours. The solution was concentrated and the residue was dissolved in N,N-dimethylformamide. To this solution at ice bath temperature was added D-biotin N-hydroxysuccinimide ester (49 mg, 0.14 mmol) and DIPEA (75 μL, 0.43 mmol). The resulting mixture was stirred at this temperature for 2 hours and then partitioned between dichloromethane and water. The organic phase was washed with water (2×) and sat. brine, dried over sodium sulfate, and concentrated to afford an oil. Purification by flash silica gel column chromatography, eluting with 7:93 methanol/dichloromethane, provided 48 (55 mg, 51%) as a pale yellow oil: (MS (ES+) m/z 757.2 (M+H)+.

1. concentrationThe solution was concentrated
2. dissolutionthe residue was dissolved in N,N-dimethylformamide
3. custompartitioned between dichloromethane and water
4. washThe organic phase was washed with water (2×) and sat. brine
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated
7. customto afford an oil
8. customPurification by flash silica gel column chromatography
9. washeluting with 7:93 methanol/dichloromethane