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Lithium hydroxide, monohydrate → HCID 86700858, Verbindung

HRID 881753
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 881753
C[O:2][C:3](=[O:35])[CH2:4][C:5]12[CH2:12][CH2:11][C:8]([C:13]3[CH:18]=[CH:17][C:16]([C:19]4[CH:24]=[CH:23][C:22]([NH:25][C:26]5[O:27][C:28]([C:31]([CH3:34])([CH3:33])[CH3:32])=[N:29][N:30]=5)=[CH:21][CH:20]=4)=[CH:15][CH:14]=3)([CH2:9][CH2:10]1)[O:7][CH2:6]2.O.[OH-].[Li+]>O1CCCC1.C(O)C.O>[C:31]([C:28]1[O:27][C:26]([NH:25][C:22]2[CH:21]=[CH:20][C:19]([C:16]3[CH:17]=[CH:18][C:13]([C:8]45[CH2:9][CH2:10][C:5]([CH2:4][C:3]([OH:35])=[O:2])([CH2:12][CH2:11]4)[CH2:6][O:7]5)=[CH:14][CH:15]=3)=[CH:24][CH:23]=2)=[N:30][N:29]=1)([CH3:34])([CH3:32])[CH3:33]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 86700856HCID 86700856, Verbindung

Produkt 1

HCID 86700858HCID 86700858, VerbindungAusbeute 71,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel
HCID 8028
Tetrahydrofuran
Lösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A 100 ml round bottom flask was charged with {1-[4′-(5-tert-butyl-[1,3,4]oxadiazol-2-ylamino)-biphenyl-4-yl]-2-oxa-bicyclo[2.2.2]oct-4-yl}-acetic acid methyl ester (0.27 g, 0.454 mmol), and lithium hydroxide monohydrate (0.229 g, 5.45 mmol) in tetrahydrofuran (20 ml), ethanol (10 ml) and water (8 ml) at room temperature. The mixture was heated at 50° C. for 2 hours. Most of the organic solvent was evaporated under vacuum and the mixture was acidified to PH=4 at 0° C. The solvents were then removed by lipherlizer. The mixture was added ethanol (40 ml) and heated to 70° C., and then was cooled to room temperature. The mixture was filtered and the solid was washed with ethanol (3 ml) and water (10 ml) to afford {1-[4′-(5-tert-butyl-[1,3,4]oxadiazol-2-ylamino)-biphenyl-4-yl]-2-oxa-bicyclo[2.2.2]oct-4-yl}-acetic acid (150 mg, 71%) as white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.64-1.89 (m, 6H) 2.00-2.13 (m, 4H) 3.85 (s, 2H) 7.42 (d, J=8.40 Hz, 2H) 7.55 (d, J=8.50 Hz, 2H) 7.62 (s, 4H) 10.46 (br. s, 1H). LC/MS, [MS+] 461.23, RT: 2.66 (Condition M).

Aufarbeitung

  1. customMost of the organic solvent was evaporated under vacuum
  2. customat 0° C
  3. customThe solvents were then removed by lipherlizer
  4. additionThe mixture was added ethanol (40 ml)
  5. temperatureheated to 70° C.
  6. temperaturewas cooled to room temperature
  7. filtrationThe mixture was filtered
  8. washthe solid was washed with ethanol (3 ml) and water (10 ml)

Quellen und Nachweise

ORD-Eintrag
ord-9f44fda6f32e4dd18d62bf412400513b
Quelldatensatz
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08993619B2

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