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

HRID 1972342Notes

Reaction equation

HRID 1972342 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][C@@H: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 66582474(3S)-3-(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)-L-alanylglycinate (3.00 g, 8.71 mmol), 10 mL of CH2Cl2, and 5 mL of TFA. After 10 min at room temperature, the mixture was concentrated then dissolved in 2N NH3 in MeOH (20 mL) and stirred at room temperature for 4 h. The reaction was then concentrated and triturated with ether to give (3S)-3-(tetrahydro-2H-pyran-4-ylmethyl)-2,5-piperazinedione (1.44 g) as a white solid.

Workup

  1. concentrationthe mixture was concentrated
  2. dissolutionthen dissolved in 2N NH3 in MeOH (20 mL)
  3. concentrationThe reaction was then concentrated
  4. customtriturated with ether

Sources & evidence

ORD record
ord-85bb563594a14f2d8c6296146aa4ca8d
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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