Lithium hydroxide, monohydrate → HCID 178524864, Verbindung

HRID 2169380Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2169380
C([O:5][C:6]([C:8]1[C:13]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:12]([OH:22])[N:11]=[C:10]([CH2:23][C:24]2([C:29]3[C:38]4[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=4)[CH:32]=[CH:31][CH:30]=3)[CH2:28][CH2:27][CH2:26][CH2:25]2)[N:9]=1)=[O:7])(C)(C)C.O[Li].O>O1CCCC1.O>[CH2:15]([O:14][C:13]1[C:8]([C:6]([OH:7])=[O:5])=[N:9][C:10]([CH2:23][C:24]2([C:29]3[C:38]4[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=4)[CH:32]=[CH:31][CH:30]=3)[CH2:28][CH2:27][CH2:26][CH2:25]2)=[N:11][C:12]=1[OH:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Komponenten

5

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 178450804HCID 178450804, Verbindung

Produkt 1

HCID 178524864HCID 178524864, VerbindungAusbeute 76,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 5-benzyloxy-6-hydroxy-2-(1-naphthalen-1-yl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid tert-butyl ester (344) (3.9 g, 7.64 mmol) in tetrahydrofuran (60 mL) and water (12 mL) was added LiOH.H2O (3.2 g, 76.4 mmol) and the reaction mixture heated to reflux for 20 h (the reaction was monitored by LC-MS), tetrahydrofuran was removed from the reaction mixture under vacuum and the residue was diluted with water (50 mL). The aqueous layer was washed with ethyl acetate (2×50 mL) and then acidified with 1N HCl to pH 3. A white solid was separated by filtration and dried in vacuum to get pure 5-benzyloxy-6-hydroxy-2-(1-naphthalen-1-yl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid (345) (2.65 g, 76%) as a white solid.

Aufarbeitung

  1. temperaturethe reaction mixture heated
  2. temperatureto reflux for 20 h (the reaction
  3. customwas removed from the reaction mixture under vacuum
  4. additionthe residue was diluted with water (50 mL)
  5. washThe aqueous layer was washed with ethyl acetate (2×50 mL)
  6. customA white solid was separated by filtration
  7. customdried in vacuum

Quellen und Nachweise

ORD-Eintrag
ord-eec40fda5bca4a34ab44ecae620599ec
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09045486B2

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