Beta-Alanine → 3-Maleimidopropionic acid

HRID 1499324노트

반응식

HRID 1499324 반응식
[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]

참가 물질

4

반응물 2

HCID 239Beta-AlanineHCID 7923Maleic Anhydride

생성물 1

HCID 5736213-Maleimidopropionic acid수율 41%

시약·촉매·용매 1

HCID 176Acetic Acid용매3회

실험 절차

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−11H NMR (400.03 MHz, CDCl3, 298 K) δ=2.69 (t, J=7.3 Hz, 211, 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.

후처리

  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)

출처 및 근거

ORD 기록
ord-684e72ca393d4c8bbb72b926e240a419
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09200104B2

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