Reacción #1591085

Ecuación de reacción

22.2

tert-butyl N-(4-[[(3S)-3-[2-[(tert-butyldimethylsilyl)oxy]ethyl]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2 (6),9,11-tetraen-12-yl]oxy]cyclohexyl)-N-methylcarbamate

Bu4NF

→

tert-butyl N-(4-[[(3S)-3-(2-hydroxyethyl)-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-12-yl]oxy]cyclohexyl)-N-methylcarbamate

Rendimiento 97.0%

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction was then quenched by the addition of water
2. 2
   Extracciónextracted with ethyl acetate (2×100 mL)
3. 3
   LavadoThe combined organic layers were washed with brine
4. 4
   Secadodried over anhydrous sodium sulfate
5. 5
   FiltraciónAfter filtration and concentration under reduced pressure
6. 6
   Otropurified

Procedimiento

A solution of 22.2 (6.5 g, 11.57 mmol, 1.00 equiv) and Bu4NF (4.5 g, 17.24 mmol, 1.49 equiv) in tetrahydrofuran (100 mL) was stirred for 2 h at room temperature. The reaction was then quenched by the addition of water and extracted with ethyl acetate (2×100 mL). The combined organic layers were washed with brine and dried over anhydrous sodium sulfate. After filtration and concentration under reduced pressure, the residue was loaded onto a silica gel column with ethyl acetate/petroleum ether (1:1) and purified to give tert-butyl N-(4-[[(3S)-3-(2-hydroxyethyl)-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-12-yl]oxy]cyclohexyl)-N-methylcarbamate (22.3, 5 g, 97%) as a yellow oil. MS: m/z 448 (M+H)+.

Fuente