Réaction #1994226

ord-cfcc9059646047e9a277c8a4ca8368a2

Équation de réaction

CC(C)(C)OC(=O)NCC(=O)O.CCCN(CCc1cccs1)[C@H]1CCc2c(O)cccc2C1.Cl
Boc-Gly Rotigotine HCl
O=C(O)C(F)(F)F
trifluoroacetic acid
CCCN(CCc1cccs1)[C@H]1CCc2c(O)cccc2C1.NCC(=O)O
Gly Rotigotine
Rendement 79.0%

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

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

Mode opératoire

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

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US08597633B2uspto-grants-2013_12