Reaction #1994226

Reaction equation

Boc-Gly Rotigotine HCl

trifluoroacetic acid

→

Gly Rotigotine

Yield 79.0%

Solvents

dichloromethane

Conditions

Workup

1. 1
   Otherall the volatiles were removed
2. 2
   Othera rotary evaporator
3. 3
   workup.DISSOLUTIONThe residue (dark yellow) was dissolved in methanol
4. 4
   Otherprecipitated
5. 5
   workup.ADDITIONby adding into diethyl ether (40 mL)
6. 6
   FiltrationThe pale yellow precipitate was filtered
7. 7
   Otherdried

Procedure

The Boc-Gly-Rotigotine HCl was deprotected by first dissolving the product (1.258 g, 2.55 mmol) in dichloromethane (64 ml). After addition of trifluoroacetic acid (9.83 ml, 128 mmol), the reaction mixture was stirred for 1 hour at room temperature and then all the volatiles were removed using a rotary evaporator. The residue (dark yellow) was dissolved in methanol and precipitated by adding into diethyl ether (40 mL). The pale yellow precipitate was filtered using a glass frit and dried to give Gly-Rotigotine.2TFA (1.140 g, 79% yield).

Source