L-Aspartic Acid → (2s)-2-{[(3-Oxo-3,4-dihydro-2-pyrazinyl)-carbonyl]amino}-butanedioic acid

HRID 2063166Notes

Reaction equation

[OH:1][C:2]1[C:3]([C:8]([O:10]C)=O)=[N:4][CH:5]=[CH:6][N:7]=1.[NH2:12][C@H:13]([C:18]([OH:20])=[O:19])[CH2:14][C:15]([OH:17])=[O:16].C(N(CC)CC)C>CS(C)=O>[O:1]=[C:2]1[NH:7][CH:6]=[CH:5][N:4]=[C:3]1[C:8]([NH:12][C@@H:13]([CH2:14][C:15]([OH:17])=[O:16])[C:18]([OH:20])=[O:19])=[O:10]

Participants

Conditions

Temperature: 50 °C

Procedure

In 4 mL of dimethyl sulfoxide is dissolved 0.4 g of methyl 3-hydroxy-2-pyrazinecarboxlate. Then, 0.27 g of L-aspartic acid and 0.85 mL of triethylamine are successively added to the solution, which is then stirred at 50° C. for 6 hours. The deposited crystals are filtered off, and the filtrate is concentrated under reduced pressure. Then, 2 mL of water and 0.2 mL of methanol are added to the resulting residue. The precipitate formed is collected by filtration to obtain 0.09 g of (2S)-2-{[(3-oxo-3,4-dihydro-2-pyrazinyl)-carbonyl]amino}-butanedioic acid.

Workup

filtrationThe deposited crystals are filtered off
concentrationthe filtrate is concentrated under reduced pressure
additionThen, 2 mL of water and 0.2 mL of methanol are added to the resulting residue
customThe precipitate formed
filtrationis collected by filtration

Sources & evidence

ORD record: ord-c6cca96cb60747b189ccc212db2454d6
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: USRE043748E1

Reaction notes

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