Acetic Acid → HCID 54495250, compound

HRID 2211243Notes

Reaction equation

HRID 2211243 reaction equation
[NH2:1][C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][C:5](=[O:7])[NH2:6].[N:11]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:17](O[C:20](=O)[C:12]=12)=O.[C:22](O)(=O)[CH3:23]>C(O)C>[N:11]1[C:12]2[C:13](=[CH:17][CH:22]=[CH:23][CH:20]=2)[CH:14]=[CH:15][C:16]=1[NH:1][C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][C:5](=[O:7])[NH2:6]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 5961L-GlutamineHCID 69688Furo[3,4-b]pyridine-5,7-dione

Product 1

HCID 54495250HCID 54495250, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred suspension of (S)-glutamine (14.6 g, 100 mL) and pyridine-2,3-dicarboxylic anhydride (14.9 g, 100 mmol) in 100 mL of acetic acid is heated at reflux for 1 hour. The resulting solution is allowed to cool. The solid which forms upon cooling is filtered and the solid washed with acetic acid and dried to afford 7.11 g (26%) of crude product. The crude product is slurried in 700 mL of refluxing ethanol, the suspension cooled, and the slurry collected by filtration and dried to afford 6.10 g (23%) of N-quinolinylglutamine, which can be alternatively named as 2-(1,3-dioxo-4-azaisoindol-2-yl)-3-carbamoylpropionic acid, as a white powder. mp 222°-226° C.; 1H NMR (dmso-d6) δ 13.25 (br s, 1 H, COOH), 9.04 (dd, 1 H, J=1.2, 4.9 Hz, pyr), 8.37 (dd, 1 H, J=1.2, 7.8 Hz, pyr), 7.85 (dd, 1 H, J=4.9, 7.8 Hz, pyr), 7.20 (s, 1 H, CONH2), 6.73 (s, 1 H, CONH2), 4.83 (dd, 1 H, J=10.2, 4.8 HZ, CHN), 2.55-1.90 (m, 4 H, CH2CH2); 13C NMR (dmso-d6) 6 1173.22, 170.21, 165.8, 165.7, 155.4, 150.9, 31.7, 128.3, 126.9, 51.5, 31.4, 24.0.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 1 hour
  3. temperatureto cool
  4. temperatureupon cooling
  5. filtrationis filtered
  6. washthe solid washed with acetic acid
  7. customdried
  8. customto afford 7.11 g (26%) of crude product
  9. temperaturethe suspension cooled
  10. filtrationthe slurry collected by filtration
  11. customdried

Sources & evidence

ORD record
ord-d2fab5dbe80745f981d7058feaf6f8ec
Source dataset
uspto-grants-1995_10
Patent number
US05463063

Reaction notes

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