Trifluoroacetic acid → Cyclo(-Gly-Phe)

HRID 1784694Notes

Reaction equation

HRID 1784694 reaction equation
C(OC(=O)[C@H:5]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[NH:6][C:7](=[O:17])[CH2:8][NH:9][C:10](OC(C)(C)C)=[O:11])C.FC(F)(F)C(O)=O>ClCCl>[CH2:18]([C@@H:5]1[NH:6][C:7](=[O:17])[CH2:8][NH:9][C:10]1=[O:11])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 11371547HCID 11371547, compound

Product 1

HCID 7076549Cyclo(-Gly-Phe)Yield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Boc-glycylphenylalanine ethyl ester (5.96 g) in dichloromethane (20 ml) was added trifluoroacetic acid (20 mL) at room temperature. After stirring 1.5 h, the resulting solution was concentrated in vacuo. The residue was dissolved in water, into which sodium bicarbonate was added until the pH was 9. After the solution was stirred for several hours, the resulting white crystals were collected and dried in vacuo to afford (S)-3-benzyl-2,5-dioxopiperazine (2.29 g, 70% in 2 steps) as a white powder.

Workup

  1. concentrationthe resulting solution was concentrated in vacuo
  2. dissolutionThe residue was dissolved in water, into which sodium bicarbonate
  3. additionwas added until the pH was 9
  4. stirringAfter the solution was stirred for several hours
  5. customthe resulting white crystals were collected
  6. customdried in vacuo

Sources & evidence

ORD record
ord-a40728b054464428beffa3efeff83f72
Source dataset
uspto-grants-2009_03
Patent number
US07504411B2

Reaction notes

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