2-Fluorobenzoyl chloride → Ataluren

HRID 450700Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 450700
C[O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10](=[NH:13])[NH:11][OH:12])[CH:5]=1.C(N(C(C)C)CC)(C)C.[F:24][C:25]1[CH:33]=[CH:32][CH:31]=[CH:30][C:26]=1[C:27](Cl)=O>C1COCC1>[F:24][C:25]1[CH:33]=[CH:32][CH:31]=[CH:30][C:26]=1[C:27]1[O:12][N:11]=[C:10]([C:6]2[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=2)[C:3]([OH:2])=[O:14])[N:13]=1

Komponenten

5

Edukt 3

HCID 98082-Fluorobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 178497860HCID 178497860, Verbindung

Produkt 1

HCID 11219835AtalurenAusbeute 91,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 3-(N-Hydroxycarbamimidoyl)-benzoic acid methyl ester (60 g, 310 mmol) in anhydrous THF (200 mL) was added diisopropylethylamine (75 mL, 434 mmol) at 5° C., and then to the mixture was added 2-fluorobenzoyl chloride (48.1 mL, 403 mmol) over 20 min. The reaction mixture was stirred forth at room temperature. The precipitate was filtered off and the filtrate was concentrated under reduced pressure. The residue was dissolved in ethylacetate (400 mL) and then washed with water (200 mL×2). The solvent was removed under reduced pressure and the desired product was crystallized in 60% ethylacetate in hexane to yield the desired product (81 g, 83% yield) as a white solid. 1H-NMR (CDCl3) δ 8.18 (1H), 8.03 (2H), 7.48 (2H), 7.18 (2H), 5.61 (2H), 3.82 (3H).

Aufarbeitung

  1. filtrationThe precipitate was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in ethylacetate (400 mL)
  4. washwashed with water (200 mL×2)
  5. customThe solvent was removed under reduced pressure
  6. customthe desired product was crystallized in 60% ethylacetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-9b120ce435a347668b4d3efe744ced02
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08486982B2

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