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Lithium hydroxide, monohydrate → {6-Chloro-3-methyl-4-[4-(4-trifluoromethoxy-phenyl-sulfamoyl)-phenyl]-naphthalen-2-yl}-acetic acid

HRID 1468410
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1468410
O.[OH-].[Li+].C[O:5][C:6](=[O:41])[CH2:7][C:8]1[C:17]([CH3:18])=[C:16]([C:19]2[CH:24]=[CH:23][C:22]([S:25](=[O:39])(=[O:38])[NH:26][C:27]3[CH:32]=[CH:31][C:30]([O:33][C:34]([F:37])([F:36])[F:35])=[CH:29][CH:28]=3)=[CH:21][CH:20]=2)[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([Cl:40])[CH:14]=2)[CH:9]=1.C1COCC1.O>CCCCCC>[Cl:40][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([CH2:7][C:6]([OH:41])=[O:5])[C:17]([CH3:18])=[C:16]2[C:19]1[CH:24]=[CH:23][C:22]([S:25](=[O:39])(=[O:38])[NH:26][C:27]2[CH:32]=[CH:31][C:30]([O:33][C:34]([F:37])([F:35])[F:36])=[CH:29][CH:28]=2)=[CH:21][CH:20]=1
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Komponenten

5

Edukt 3

HCID 168937Lithium hydroxide, monohydrateHCID 21881883Oxolane--water (1/1)HCID 86695003{6-Chloro-3-methyl-4-[4-(4-trifluoromethoxy-phenylsulfamoyl)-phenyl]-naphthalen-2-yl}-acetic acid methyl ester

Produkt 1

HCID 71711194{6-Chloro-3-methyl-4-[4-(4-trifluoromethoxy-phenyl-sulfamoyl)-phenyl]-naphthalen-2-yl}-acetic acidAusbeute 72,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8058HexaneLösungsmittel

Versuchsvorschrift

Lithium hydroxide monohydrate (0.009 g, 0.21 mmol) was added to a stirred solution of {6-chloro-3-methyl-4-[4-(4-trifluoromethoxy-phenylsulfamoyl)-phenyl]-naphthalen-2-yl}-acetic acid methyl ester (0.030 g, 0.05 mmol) in a 3:1 mixture of THF—H2O mixture (5 mL). The reaction mixture was stirred for 16 hours at room temperature. The reaction mixture was concentrated to remove THF, and the crude material was diluted with water, acidified [pH˜2] with a 6 N aqueous solution of hydrochloric acid. The mixture was extracted twice with ethyl acetate. The collected organic layers were washed with water and brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure to give the crude product. Trituration with hexane afforded {6-chloro-3-methyl-4-[4-(4-trifluoromethoxy-phenyl-sulfamoyl)-phenyl]-naphthalen-2-yl}-acetic acid (0.02 g, 69%) as a solid. 1H NMR (DMSO-d6) δ: 12.49 (br. s, 1H), 10.56 (br. s, 1H), 7.82-8.03 (m, 4H), 7.38-7.54 (m, 3H), 7.27-7.35 (m, 2H), 7.19-7.27 (m, 2H), 6.82 (s, 1H), 3.84 (s, 2H), 1.99 (s, 3H). MS calcd. for C26H18ClF3NO5S [(M−H)−] 548, obsd. 548.0.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. customto remove THF
  3. additionthe crude material was diluted with water
  4. extractionThe mixture was extracted twice with ethyl acetate
  5. washThe collected organic layers were washed with water and brine
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customto give the crude product

Quellen und Nachweise

ORD-Eintrag
ord-b3954115493f4a818d238b1e28dd62d7
Quelldatensatz
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09000044B2

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