Trifluoroacetic acid → HCID 131730239, compound

HRID 1907044Notes

Reaction equation

HRID 1907044 reaction equation
[NH:1](C(OC(C)(C)C)=O)[CH2:2][C:3]([OH:5])=[O:4].[CH3:13][CH2:14][CH2:15][N:16]([C@@H:24]1[CH2:29][C:28]2[CH:30]=[CH:31][CH:32]=[C:33]([OH:34])[C:27]=2[CH2:26][CH2:25]1)[CH2:17][CH2:18][C:19]1[S:23][CH:22]=[CH:21][CH:20]=1.Cl.FC(F)(F)C(O)=O>ClCCl>[NH2:1][CH2:2][C:3]([OH:5])=[O:4].[CH3:13][CH2:14][CH2:15][N:16]([C@@H:24]1[CH2:29][C:28]2[CH:30]=[CH:31][CH:32]=[C:33]([OH:34])[C:27]=2[CH2:26][CH2:25]1)[CH2:17][CH2:18][C:19]1[S:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131730240HCID 131730240, compound

Product 1

HCID 131730239HCID 131730239, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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).

Workup

  1. customall the volatiles were removed
  2. customa rotary evaporator
  3. dissolutionThe residue (dark yellow) was dissolved in methanol
  4. customprecipitated
  5. additionby adding into diethyl ether (40 mL)
  6. filtrationThe pale yellow precipitate was filtered
  7. customdried

Sources & evidence

ORD record
ord-cfcc9059646047e9a277c8a4ca8368a2
Source dataset
uspto-grants-2013_12
Patent number
US08597633B2

Reaction notes

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