Maleic Anhydride → HCID 53248105, compound

HRID 882670Notes

Reaction equation

HRID 882670 reaction equation
[NH2:1][CH2:2][CH:3]([S:8]([OH:11])(=[O:10])=[O:9])[CH2:4][C:5]([OH:7])=[O:6].[C:12]1(=[O:18])[O:17][C:15](=[O:16])[CH:14]=[CH:13]1>CC(N(C)C)=O>[C:5]([CH2:4][CH:3]([S:8]([OH:11])(=[O:9])=[O:10])[CH2:2][NH:1][C:12](=[O:18])/[CH:13]=[CH:14]\[C:15]([OH:17])=[O:16])([OH:7])=[O:6]

Participants

4

Reactant 2

HCID 7923Maleic AnhydrideHCID 20561417HCID 20561417, compound

Product 1

HCID 53248105HCID 53248105, compoundYield 86.9%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To the solution of 4-amino-3-sulfobutanoic acid (˜2.50 g, 13.66 mmol) in 100 ml of DMA was added maleic anhydride (1.48 g, 15.10 mmol) and the mixture was stirred over night, evaporated, purified on C-18 column (2×30 cm) eluted with 1% HAc in water and crystallized with MeOH/Acetone/toluene to afford 3.34 g (83%) of (Z)-4-(3-carboxy-2-sulfopropylamino)-4-oxobut-2-enoic acid. 1H NMR (CD3OD) 6.33 (d, 1H, J=12.6 Hz), 6.10 (d, 1H, J=12.6 Hz), 3.64 (dd, 1H, J=5.8, 14.0 Hz), 3.54 (m, 1H), 3.30 (m, 1H), 2.78 (dd, 1H, J=4.9, 16.8 Hz), 2.39 (m, 1H); 13C NMR 173.52, 168.68, 167.98, 135.59, 127.79, 57.31, 40.56, 34.52; ESI MS m/z−279.7 (M−H).

Workup

  1. customevaporated
  2. custompurified on C-18 column (2×30 cm)
  3. washeluted with 1% HAc in water
  4. customcrystallized with MeOH/Acetone/toluene

Sources & evidence

ORD record
ord-736abaeaa05540a08f62b6291063e003
Source dataset
uspto-grants-2012_08
Patent number
US08236319B2

Reaction notes

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