Sodium Hydroxide → Ivacaftor carboxylate

HRID 1915108Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1915108
[C:1]([C:5]1[C:6]([NH:17][C:18]([C:20]2[C:29](=[O:30])[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[NH:22][CH:21]=2)=[O:19])=[CH:7][C:8]2[O:12][C:11](=[O:13])[C:10]([CH3:15])([CH3:14])[C:9]=2[CH:16]=1)([CH3:4])([CH3:3])[CH3:2].[OH-:31].[Na+]>CO>[C:1]([C:5]1[C:6]([NH:17][C:18]([C:20]2[C:29](=[O:30])[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[NH:22][CH:21]=2)=[O:19])=[CH:7][C:8]([OH:31])=[C:9]([C:10]([CH3:15])([CH3:14])[C:11]([OH:12])=[O:13])[CH:16]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 59544159N-(5-(tert-Butyl)-3,3-dimethyl-2-oxo-2,3-dihydrobenzofuran-6-yl)-4-oxo-1,4-dihydroquinoline-3-carboxamide

Produkt 1

HCID 46917263Ivacaftor carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To a stirred solution of compound 21 (0.9 g, 2.45 mmol) in MeOH (50 mL) was added NaOH (1.5 g, 37.5 mmol) at 0° C. After stirring for 16 hours at 40° C., the solvent was evaporated in vacuo, then the residue was dissolved in H2O (50 ml). The precipitate was filtered and the filtrate was washed with DCM (100 mL×1) and ethyl acetate (100 mL×1). The aqueous layer was acidified with 2N HCl to pH 1-2. The precipitate was filtered and washed with H2O (80 mL) and heptane (50 mL). It was dried in vacuo to give compound 28 as a white solid. 1H NMR (DMSO-d6; 400 MHz) δ 12.85 (s), δ 11.84 (s), δ 11.77 (s), δ 9.39 (s), δ 8.86 (s), δ 8.33 (s), δ 7.79 (m), δ 7.52 (m), δ 7.18 (s), δ 7.09 (s), δ 1.44 (s), δ 1.40 (s). MS found (M+H) 423.08

Aufarbeitung

  1. customthe solvent was evaporated in vacuo
  2. dissolutionthe residue was dissolved in H2O (50 ml)
  3. filtrationThe precipitate was filtered
  4. washthe filtrate was washed with DCM (100 mL×1) and ethyl acetate (100 mL×1)
  5. filtrationThe precipitate was filtered
  6. washwashed with H2O (80 mL) and heptane (50 mL)
  7. customIt was dried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-60b1a6ed1d164fa3aef352d304dd2528
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08614325B2

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