Benzenesulfonyl chloride → [4-(4-Benzenesulfonylamino-phenyl)-6-fluoro-3-methyl-naphthalen-2-yl]-acetic acid methyl ester

HRID 1468450Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1468450
[CH3:1][O:2][C:3](=[O:24])[CH2:4][C:5]1[C:14]([CH3:15])=[C:13]([C:16]2[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:23])[CH:11]=2)[CH:6]=1.[C:25]1([S:31](Cl)(=[O:33])=[O:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(N(C(C)C)CC)(C)C>C1COCC1>[CH3:1][O:2][C:3](=[O:24])[CH2:4][C:5]1[C:14]([CH3:15])=[C:13]([C:16]2[CH:21]=[CH:20][C:19]([NH:22][S:31]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)(=[O:33])=[O:32])=[CH:18][CH:17]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:23])[CH:11]=2)[CH:6]=1

Komponenten

5

Edukt 3

HCID 7369Benzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 86694944[4-(4-Amino-phenyl)-6-fluoro-3-methyl-naphthalen-2-yl]-acetic acid methyl ester

Produkt 1

HCID 86695029[4-(4-Benzenesulfonylamino-phenyl)-6-fluoro-3-methyl-naphthalen-2-yl]-acetic acid methyl esterAusbeute 48,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of [4-(4-amino-phenyl)-6-fluoro-3-methyl-naphthalen-2-yl]-acetic acid methyl ester (55 mg, 0.17 mmol) and benzenesulfonyl chloride (61 mg, 0.34 mmol) in THF (3 mL) was added diisopropylethylamine (62 mg, 0.49 mmol) at 0° C. under nitrogen. The reaction mixture was warmed to room temperature and stirred for 3 hours. The solvent was removed under vacuum and the residue was diluted with water (10 mL). The mixture was extracted with ethyl acetate (2×20 mL). The combined organic extracts were washed with brine solution (50 mL) and dried over anhydrous magnesium sulfate. Filtration of the drying agent and concentration of the solvent under vacuum gave the crude residue which was purified using an ISCO (12 g) column, eluting with 2-25% ethyl acetate in hexanes, to afford [4-(4-benzenesulfonylamino-phenyl)-6-fluoro-3-methyl-naphthalen-2-yl]-acetic acid methyl ester (38 mg, 48%) as a white solid. 1H NMR (300 MHz, CDCl3) δ ppm 7.84 (d, J=7.5 Hz, 2 H), 7.77 (dd, J=9.1, 6.0 Hz, 1 H), 7.70 (s, 1 H), 7.59 (t, J=7.5 Hz, 1 H), 7.49 (t, J=7.5 Hz, 2 H), 7.15-7.22 (m, 3 H), 7.10 (d, J=8.2 Hz, 2 H), 6.80 (s, 1 H), 6.71 (dd, J=11.3, 2.3 Hz, 1 H), 3.78-3.90 (m, 2 H), 3.73 (s, 3 H), 2.09 (s, 3 H). HRMS calcd. for C26H21FNO4S [(M−H)−] 462.1181, obsd. 462.1179.

Aufarbeitung

  1. customThe solvent was removed under vacuum
  2. additionthe residue was diluted with water (10 mL)
  3. extractionThe mixture was extracted with ethyl acetate (2×20 mL)
  4. washThe combined organic extracts were washed with brine solution (50 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationFiltration of the drying agent and concentration of the solvent under vacuum
  7. customgave the crude residue which
  8. customwas purified
  9. washeluting with 2-25% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-ea825415ceb7466da700792977800bd1
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09000044B2

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