Reaction #1340595

Reaction equation

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

Solvents

H2O

Conditions

Workup

1. 1
   Otherresulted in a colourless suspension
2. 2
   OtherDCM 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
   DryingThe latter combined organic layers were dried over MgSO4
6. 6
   Concentrationconcentrated under reduced pressure
7. 7
   Otherwas subjected to the next step without further purification

Procedure

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