L-Glutamine → HCID 9860418, compound

HRID 1417359Notes

Reaction equation

HRID 1417359 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:19][C:20](=O)[C:12]=12)=[O:18]>C(O)(=O)C>[O:18]=[C:17]1[C:13]2[C:12](=[N:11][CH:16]=[CH:15][CH:14]=2)[C:20](=[O:19])[N:1]1[CH:2]([CH2:3][CH2:4][C:5]([NH2:6])=[O:7])[C:8]([OH:10])=[O:9]

Participants

4

Reactant 2

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

Product 1

HCID 9860418HCID 9860418, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A stirred suspension of (S)-glutamine (14.6 g, 100 mmol) and 2,3-pyridinedicarboxylic anhydride (14.9 g, 100 mmol) in 100 mL of acetic acid is heated and refluxed for 1 hour. The reaction solution is cooled to form a solid. The solid is removed by filtration and washed with acetic acid to yield 7.11 g (26%) of 2-(1,3-dioxo-4-azaisoindolin-2-yl)glutaramic acid. The product can be further purified by slurring in 700 mL of refluxing ethanol, cooling, filtering, and drying to produce a white powder with a melting point of 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) δ 1173.22, 170.21, 165.8, 165.7, 155.4, 150.9, 131.7, 128.3, 126.9, 51.5, 31.4, 24.0.

Workup

  1. temperatureis heated
  2. temperaturerefluxed for 1 hour
  3. temperatureThe reaction solution is cooled
  4. customto form a solid
  5. customThe solid is removed by filtration
  6. washwashed with acetic acid

Sources & evidence

ORD record
ord-bcf1418fa4354386891ad1ec6544c2db
Source dataset
uspto-grants-1999_03
Patent number
US05877200

Reaction notes

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