Triethylamine → (2S)-2-[((2S)-2-{[(3-oxo-3,4-dihydro-2-pyrazinyl)carbonyl]amino}-propanoyl)amino]propanoic acid

HRID 1005752Notes

Reaction equation

HRID 1005752 reaction equation
FC(F)(F)C(O)=O.[NH2:8][C@H:9]([C:11]([NH:13][C@H:14]([C:16]([OH:18])=[O:17])[CH3:15])=[O:12])[CH3:10].C(N(CC)CC)C.[OH:26][C:27]1[C:28]([C:33](OC)=[O:34])=[N:29][CH:30]=[CH:31][N:32]=1>CS(C)=O>[O:26]=[C:27]1[NH:32][CH:31]=[CH:30][N:29]=[C:28]1[C:33]([NH:8][C@@H:9]([CH3:10])[C:11]([NH:13][C@@H:14]([CH3:15])[C:16]([OH:18])=[O:17])=[O:12])=[O:34]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 49796171L-alanyl-L-alanine trifluoroacetateHCID 178499100HCID 178499100, compound

Product 1

HCID 69380637(2S)-2-[((2S)-2-{[(3-oxo-3,4-dihydro-2-pyrazinyl)carbonyl]amino}-propanoyl)amino]propanoic acidYield 8.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
40 °C

Procedure

In 5 mL of dimethyl sulfoxide is dissolved 0.42 g of L-alanyl-L-alanine trifluoroacetate. Then, 1.07 mL of triethylamine and 0.71 g of methyl 3-hydroxy-2-pyrazinecarboxylate are successively added to the solution, which is then stirred at 40° C. for 17 hours. The solvent is distilled off under reduced pressure, and 2 mL of water was added to the residue thus obtained. The deposited product is collected by filtration and purified by column chromatography [eluent: chloroform:methanol=30:1) to obtain 0.035 g of (2S)-2-[((2S)-2-{[(3-oxo-3,4-dihydro-2-pyrazinyl)carbonyl]amino}-propanoyl)amino]propanoic acid.

Workup

  1. distillationThe solvent is distilled off under reduced pressure, and 2 mL of water
  2. additionwas added to the residue
  3. customthus obtained
  4. filtrationThe deposited product is collected by filtration
  5. custompurified by column chromatography [eluent

Sources & evidence

ORD record
ord-1ceea5564f2142f19c668de048c56fe8
Source dataset
uspto-grants-2004_09
Patent number
US06787544B2

Reaction notes

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