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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 55748Erstellt: 24. Oktober 2026

3-Acetamidophthalic Anhydride → Apremilast, (+-)-

https://huagongshe.com/de/reaction/55748

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
Edukt3-Acetamidophthalic AnhydrideHCID 226121—
Edukt1-(3-Ethoxy-4-methoxy-phenyl)-2-methanesulfonyl-ethylamineHCID 11288792—
LösungsmittelAcetic AcidHCID 176—
ProduktApremilast, (+-)-HCID 1015171559,3%

Reaktionsschritte

A stirred solution of 1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethylamine (1.0 g, 3.7 mmol) and 3-acetamidophthalic anhydride (751 mg, 3.66 mmol) in acetic acid (20 mL) was heated at reflux for 15 h. The solvent was removed in vacuo to yield an oil. Chromatography of the resulting oil yielded the product as a yellow solid (1.0 g, 59% yield): mp, 144° C.; 1H NMR (CDCl3) δ: 1.47 (t, J=7.0 Hz, 3H, CH3), 2.26 (s, 3H, CH3), 2.88 (s, 3H, CH3), 3.75 (dd, J=4.4, 14.3 Hz, 1H, CH), 3.85 (s, 3H, CH3), 4.11 (q, J=7 Hz, 2H, CH2), 5.87 (dd, J=4.3, 10.5 Hz, 1H, NCH), 6.82-6.86 (m, 1H, Ar), 7.09-7.11 (m, 2H, Ar), 7.47 (d, J=7 Hz, 1H, Ar), 7.64 (t, J=8 Hz, 1H, Ar), 8.74 (d, J=8 Hz, 1H, Ar), 9.49 (br s, 1H, NH); 13C NMR (CDCl3) δ: 14.61, 24.85, 41.54, 48.44, 54.34, 55.85, 64.43, 111.37, 112.34, 115.04, 118.11, 120.21, 124.85, 129.17, 130.96, 136.01, 137.52, 148.54, 149.65, 167.38, 169.09, 169.40; Anal Calc'd. for C22H24NO7S: C, 57.38; H, 5.25; N, 6.08. Found: C, 57.31; H, 5.34; N, 5.83.

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS09433606B2
Quelldatensatzuspto-grants-2016_09
ORD IDord-fa1809e0e791470aac87ca872f0d4638
Quellennotizuspto-grants-2016_09