Reacción #1340595

Ecuación de reacción

amine

(S,E)-tert-butyl 4-(4-(methylsulfonyl)-2-(tritylamino)but-3-en-1-yl)benzylcarbamate

TFA DCM

HCl

→

(S,E)-tert-butyl 4-(4-(methylsulfonyl)-2-aminobut-3-en-1-yl)benzylcarbamate

Disolventes

H2O

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroresulted in a colourless suspension
2. 2
   OtroDCM was removed under reduced pressure
3. 3
   ExtracciónThe aqueous layer was extracted with Et2O (3×)
4. 4
   Extracciónafter which it was extracted with DCM (3×)
5. 5
   SecadoThe latter combined organic layers were dried over MgSO4
6. 6
   Concentraciónconcentrated under reduced pressure
7. 7
   Otrowas subjected to the next step without further purification

Procedimiento

Trityl protected amine 17 (0.54 g, 0.90 mmol) was treated with 1% v/v TFA/DCM (15 mL) at room temperature. To this yellow solution was added H2O (1 mL) which resulted in a colourless suspension. After stirring the mixture for 30 minutes, 10 mM aq. HCl (20 mL) was added and DCM was removed under reduced pressure. The aqueous layer was extracted with Et2O (3×) and basified with NaHCO3 until pH 9, after which it was extracted with DCM (3×). The latter combined organic layers were dried over MgSO4 and concentrated under reduced pressure. The resulting deprotected amine proved to be pure on LC-MS analysis and was subjected to the next step without further purification.

Fuente