Reaction #969852

ord-736abaeaa05540a08f62b6291063e003

Reaction equation

NCC(CC(=O)O)S(=O)(=O)O
4-amino-3-sulfobutanoic acid
O=C1C=CC(=O)O1
maleic anhydride
→
O=C(O)/C=C\C(=O)NCC(CC(=O)O)S(=O)(=O)O
(Z)-4-(3-carboxy-2-sulfopropylamino)-4-oxobut-2-enoic acid
Yield 86.9%

Reactants

NCC(CC(=O)O)S(=O)(=O)O
4-amino-3-sulfobutanoic acid
O=C1C=CC(=O)O1
maleic anhydride

Reagents

None

Solvents

CC(=O)N(C)C
DMA

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherevaporated
  2. 2
    Otherpurified on C-18 column (2×30 cm)
  3. 3
    Washeluted with 1% HAc in water
  4. 4
    Othercrystallized with MeOH/Acetone/toluene

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).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08236319B2uspto-grants-2012_08