Beta-Alanine → 3-Maleimidopropionic acid

HRID 2090077Notes

Reaction equation

HRID 2090077 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=O)[CH:3]=[CH:2]1.[NH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12]>C(O)(=O)C>[O:7]=[C:1]1[CH:2]=[CH:3][C:4](=[O:6])[N:8]1[CH2:9][CH2:10][C:11]([OH:13])=[O:12]

Participants

4

Reactant 2

HCID 239Beta-AlanineHCID 7923Maleic Anhydride

Product 1

HCID 5736213-Maleimidopropionic acidYield 41%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent3×

Procedure

A solution of maleic anhydride (5.00 g, 0.0561 mol) in acetic acid (70 ml) was added dropwise to a solution of β-alanine (5.50 g, 0.0561 mol) in acetic acid (25 ml) and the mixture was stirred at room temperature for three hours. 50 mL of acetic acid was added to the white suspension and the mixture heated up to 115° C. After 1 h a limpid colourless solution was observed. The mixture was then stirred at this temperature overnight and the colour turned to orange. The solvent was then removed under reduced pressure and 30 mL of toluene was then added to the resulting orange oil. This was then evaporated under reduced pressure and this operation was repeated 3 times. The orange residue was then purified by flash chromatography (CC, SiO2, CH2Cl2/ethyl acetate 9:1) to give the product as a white solid (3.86 g, 0.0228 mol, 41%). m.p. 105-107° C. IR (neat): 3092, 2883, 2537, 1695, 1445, 1411, 1373, 1337, 1305, 1230, 1151, 1081, 1043, 924, 830, 773, 694, 618 cm−1. 1H NMR (400.03 MHz, CDCl3, 298 K) δ=2.69 (t, J=7.3 Hz, 2H, CH2), 3.82 (t, J=7.3 Hz, 2H, CH2), 6.71 (s, 2H, CHvinyl) 10.07 (bs, 1H, COOH). 13C{1H} NMR (100.59 MHz, CDCl3, 298 K) δ=32.62 (1C, CH2), 33.36 (1C, CH2), 134.38 (2C, CHvinyl) 170.48 (1C, C), 176.64 (2C, C). Anal. Calcd. for C7H7NO4: C, 49.71; H, 4.17; N, 8.28. Found C, 49.35; H, 4.19; N, 7.95.

Workup

  1. temperaturethe mixture heated up to 115° C
  2. waitAfter 1 h a limpid colourless solution was observed
  3. stirringThe mixture was then stirred at this temperature overnight
  4. customThe solvent was then removed under reduced pressure and 30 mL of toluene
  5. additionwas then added to the resulting orange oil
  6. customThis was then evaporated under reduced pressure
  7. customThe orange residue was then purified by flash chromatography (CC, SiO2, CH2Cl2/ethyl acetate 9:1)

Sources & evidence

ORD record
ord-85b80445100c49d6bbe8f3878279c9db
Source dataset
uspto-grants-2013_05
Patent number
US08436104B2

Reaction notes

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