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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 32778Erstellt: 24. Oktober 2026

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

https://huagongshe.com/de/reaction/32778

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) δ1.47 (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, CHH), 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) δ14.61, 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
PatentnummerUS07427638B2
Quelldatensatzuspto-grants-2008_09
ORD IDord-4b57b5c1ee914af6a3434aff4a105db8
Quellennotizuspto-grants-2008_09