Réaction #1340595

Équation de réaction

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

Solvants

H2O

Conditions de réaction

Traitement

1. 1
   Autreresulted in a colourless suspension
2. 2
   AutreDCM was removed under reduced pressure
3. 3
   ExtractionThe aqueous layer was extracted with Et2O (3×)
4. 4
   Extractionafter which it was extracted with DCM (3×)
5. 5
   SéchageThe latter combined organic layers were dried over MgSO4
6. 6
   Concentrationconcentrated under reduced pressure
7. 7
   Autrewas subjected to the next step without further purification

Mode opératoire

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.

Source