Trifluoroacetic acid → Cyclo(prolylglycyl)

HRID 456411Notes

Reaction equation

HRID 456411 reaction equation
C(N(CC)CC)C.FC(F)(F)C(O)=O.CO[C:17](=[O:27])[CH2:18][NH:19][C:20]([C@@H:22]1[CH2:26][CH2:25][CH2:24][NH:23]1)=[O:21]>CO>[C:20]1(=[O:21])[NH:19][CH2:18][C:17](=[O:27])[N:23]2[CH2:24][CH2:25][CH2:26][C@@H:22]12

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 11622459methyl 2-{[(2S)-pyrrolidin-2-yl]formamido}acetate

Product 1

HCID 126154Cyclo(prolylglycyl)Yield 34.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Triethylamine (75 ml, 540 mmol) was added to a solution of the crude trifluoroacetic acid salt of [((S)-pyrrolidine-2-carbonyl)amino]acetic acid methyl ester (15.4 g), which was isolated in the previous step, in methanol (300 ml). The reaction mixture was heated to reflux for 16 hours. It was cooled to room temperature. The solvent was removed in vacuo. The residue was suspended in 2-propanol (150 ml). The precipitation was isolated and dried in vacuo to give 4.38 g of (S)-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 16 hours
  3. customThe solvent was removed in vacuo
  4. customThe precipitation
  5. customwas isolated
  6. customdried in vacuo

Sources & evidence

ORD record
ord-b5c6159fc4454bdf86ce32a1a57a7e84
Source dataset
uspto-grants-2007_03
Patent number
US07186721B2

Reaction notes

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