Lithium Hydroxide → HCID 67983850, Verbindung

HRID 1748221Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1748221
[CH:1]1([C:4]2[O:8][N:7]=[C:6]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[O:15][C:16]([F:19])([F:18])[F:17])[C:5]=2[CH2:20][O:21][CH:22]2[CH2:28][CH:27]3[N:29]([C:30]4[CH:42]=[CH:41][C:33]5[C:34]([C:37]([O:39]C)=[O:38])=[N:35][S:36][C:32]=5[CH:31]=4)[CH:24]([CH2:25][CH2:26]3)[CH2:23]2)[CH2:3][CH2:2]1.[Li+].[OH-]>C1COCC1.CO.O>[CH:1]1([C:4]2[O:8][N:7]=[C:6]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[O:15][C:16]([F:17])([F:19])[F:18])[C:5]=2[CH2:20][O:21][CH:22]2[CH2:28][CH:27]3[N:29]([C:30]4[CH:42]=[CH:41][C:33]5[C:34]([C:37]([OH:39])=[O:38])=[N:35][S:36][C:32]=5[CH:31]=4)[CH:24]([CH2:25][CH2:26]3)[CH2:23]2)[CH2:3][CH2:2]1

Komponenten

4

Edukt 2

HCID 3939Lithium HydroxideHCID 67983726HCID 67983726, Verbindung

Produkt 1

HCID 67983850HCID 67983850, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21892291Methanol tetrahydrofuran waterLösungsmittel

Versuchsvorschrift

Methyl 6-(3-((5-cyclopropyl-3-(2-(trifluoromethoxy)phenyl)isoxazol-4-yl)methoxy)-8-azabicyclo[3.2.1]octan-8-yl)benzo[d]isothiazole-3-carboxylate (37 mg, 0.062 mg) in a 3:2:1 THF-MeOH—H2O solution (1 mL) was treated with a 6N LiOH solution (85 μL, 0.49 mmol) at rt for 12 hours. After this time the organic was removed in vacuo and the residue was diluted with water (1 mL.) and cooled in ice. 3N NaOH was added dropwise until pH 7. The solid that separated was collected by filtration, washed with additional water and dried in vacuo to afford the 6-(3-((5-cyclopropyl-3-(2-(trifluoromethoxy)phenyl)isoxazol-4-yl)methoxy)-8-azabicyclo[3.2.1]octan-8-yl)benzo[d]isothiazole-3-carboxylic acid as off white solid. 1H NMR (400 MHz, DMSO) δ 8.31 (d, J=8.0 Hz, 1H), 7.68-7.62 (m, 2H), 7.57-7.52 (m, 2H), 7.18 (bs, 1H), 6.90 (d, J=9.2 Hz, 1H), 4.31 (s, 2H), 4.18 (bs, 2H), 3.42 (m, 1H), 1.88-1.84 (m, 2H), 1.80 (1.78 (m, 4H), 1.53-1.49 (m, 2H), 1.15-1.03 (m, 5H). MS m/z 586.2 (M+1).

Aufarbeitung

  1. customAfter this time the organic was removed in vacuo
  2. additionthe residue was diluted with water (1 mL.)
  3. temperaturecooled in ice
  4. addition3N NaOH was added dropwise until pH 7
  5. customThe solid that separated
  6. filtrationwas collected by filtration
  7. washwashed with additional water
  8. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-bc2b47419b6642e6a62b233b6164f2c0
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09150568B2

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