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Lithium hydroxide, monohydrate → HCID 71711446, Verbindung

HRID 1468424
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1468424
O.[OH-].[Li+].C[O:5][C:6](=[O:42])[CH2:7][C:8]1[C:17]([CH3:18])=[C:16]([C:19]2[CH:24]=[CH:23][C:22]([S:25](=[O:40])(=[O:39])[N:26]([CH:36]([CH3:38])[CH3:37])[CH2:27][C:28]3[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=3)=[CH:21][CH:20]=2)[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([Cl:41])[CH:14]=2)[CH:9]=1.C1COCC1.O>CCCCCC>[Cl:41][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([CH2:7][C:6]([OH:42])=[O:5])[C:17]([CH3:18])=[C:16]2[C:19]1[CH:20]=[CH:21][C:22]([S:25](=[O:39])(=[O:40])[N:26]([CH:36]([CH3:38])[CH3:37])[CH2:27][C:28]2[CH:29]=[CH:30][C:31]([O:34][CH3:35])=[CH:32][CH:33]=2)=[CH:23][CH:24]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 168937Lithium hydroxide, monohydrateHCID 21881883Oxolane--water (1/1)HCID 86695013HCID 86695013, Verbindung

Produkt 1

HCID 71711446HCID 71711446, VerbindungAusbeute 86,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8058HexaneLösungsmittel

Versuchsvorschrift

Lithium hydroxide monohydrate (0.034 g, 0.80 mmol) was added to a solution of (6-chloro-4-{4-[isopropyl-(4-methoxy-benzyl)-sulfamoyl]-phenyl}-3-methyl-naphthalen-2-yl)-acetic acid methyl ester (0.115 g, 0.20 mmol) in a 3:1 mixture of THF—H2O mixture (15 mL). The reaction mixture was stirred for 16 hours at room temperature. The reaction mixture was concentrated to remove the 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 gave (6-chloro-4-{4-[isopropyl-(4-methoxy-benzyl)-sulfamoyl]-phenyl}-3-methyl-naphthalen-2-yl)-acetic acid (0.096 g, 86%) as a solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.51 (br. s, 1 H), 8.01 (d, J=8.31 Hz, 2 H), 7.98 (d, J=8.80 Hz, 1 H), 7.92 (s, 1 H), 7.46-7.52 (m, 3 H), 7.34 (d, J=8.80 Hz, 2 H), 7.00 (s, 1 H), 6.91 (d, J=8.80 Hz, 2 H), 4.43 (s, 2 H), 4.13 (spt, J=6.60 Hz, 1 H), 3.87 (s, 2 H), 3.74 (s, 3 H), 2.08 (s, 3 H), 0.93 (d, J=6.85 Hz, 6 H). MS calcd. for C30H29ClNO2S [(M−H)−] 550, obsd. 550.2.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. customto remove the 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-6d14898496674d838f22443cde62e6cd
Quelldatensatz
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09000044B2

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