Trifluoroacetic acid → Cyclo(prolylglycyl)

HRID 1071318Notes

Reaction equation

HRID 1071318 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-5aa1741f30e546788ce21b21335403a9
Source dataset
uspto-grants-2005_06
Patent number
US06906060B2

Reaction notes

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