تفاعل #1340595

معادلة التفاعل

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

المذيبات

H2O

ظروف التفاعل

المعالجة

1. 1
   أخرىresulted in a colourless suspension
2. 2
   أخرىDCM was removed under reduced pressure
3. 3
   استخلاصThe aqueous layer was extracted with Et2O (3×)
4. 4
   استخلاصafter which it was extracted with DCM (3×)
5. 5
   تجفيفThe latter combined organic layers were dried over MgSO4
6. 6
   تركيزconcentrated under reduced pressure
7. 7
   أخرىwas subjected to the next step without further purification

الإجراء التجريبي

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.

المصدر