Trifluoroacetic acid → 3-(tetrahydro-2H-pyran-4-ylmethyl)-2,5-piperazinedione

HRID 1972390Notes

Reaction equation

HRID 1972390 reaction equation
C(OC([NH:8][C@H:9]([C:17]([NH:19][CH2:20][C:21]([O:23]C)=O)=[O:18])[CH2:10][CH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[O:14]1[CH2:13][CH2:12][CH:11]([CH2:10][CH:9]2[NH:8][C:21](=[O:23])[CH2:20][NH:19][C:17]2=[O:18])[CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66582350methyl N-(tert-butoxycarbonyl)-3-(tetrahydro-2H-pyran-4-yl)-L-alanylglycinate

Product 1

HCID 665824983-(tetrahydro-2H-pyran-4-ylmethyl)-2,5-piperazinedioneYield 77.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 250 mL round-bottomed flask was charged with methyl N-(tert-butoxycarbonyl)-3-(tetrahydro-2H-pyran-4-yl)-alanylglycinate (3.00 g, 8.71 mmol), 10 mL of CH2Cl2, and 5 mL of TFA. After 10 min, the mixture was concentrated then re-dissolved in MeOH (50 mL) and triethylamine (10 mL) and then heated at reflux for 18 h. After that time, the white precipitate formed was collected by filtration to give 3-(tetrahydro-2H-pyran-4-ylmethyl)-2,5-piperazinedione (1.44 g) as a white solid.

Workup

  1. concentrationthe mixture was concentrated
  2. dissolutionthen re-dissolved in MeOH (50 mL)
  3. temperaturetriethylamine (10 mL) and then heated
  4. temperatureat reflux for 18 h
  5. customAfter that time, the white precipitate formed
  6. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-07cb484798a040cfaf1d5c6083298acb
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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