Lithium hydroxide, monohydrate → HCID 60133249, Verbindung

HRID 1472222Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1472222
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:26][CH:27]=[CH2:28])[CH:9]([C:13]2[CH:25]=[CH:24][C:16]([C:17]([O:19]CCCC)=[O:18])=[CH:15][CH:14]=2)[CH2:10][CH2:11][CH3:12])=[CH:4][CH:3]=1.O.[OH-].[Li+]>C1COCC1.CO.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([CH2:26][CH:27]=[CH2:28])[C@@H:9]([C:13]2[CH:14]=[CH:15][C:16]([C:17]([OH:19])=[O:18])=[CH:24][CH:25]=2)[CH2:10][CH2:11][CH3:12])=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 86619549HCID 86619549, Verbindung

Produkt 1

HCID 60133249HCID 60133249, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21892291Methanol tetrahydrofuran waterLösungsmittel

Versuchsvorschrift

A THF/MeOH/water (8 ml/8 ml/3 ml) solution containing the intermediate from Step F (790 mg, 1.98 mmol) and lithium hydroxide monohydrate (406 mg, 9.90 mmol) was stirred overnight at room temperature. The solution was concentrated and the nonvolatile portion was partitioned between aqueous 2N hydrochloric acid and EtOAc. The organic phase was dried over Na2SO4, filtered and concentrated to give the title compound. 1H NMR (500 MHz, DMSO-d6): δ 7.90 (d, J=8.2 Hz, 2 H); 7.39 (d, J=8.5 Hz, 2 H); 7.36 (d, J=8.5 Hz, 2H); 7.26 (d, J=8.4 Hz, 2 H); 5.36-5.26 (m, 1 H); 4.71-4.60 (m, 2 H); 2.94-2.84 (m, 2 H); 2.13-2.07 (m, 1 H); 1.95-1.87 (m, 1 H); 1.42-1.34 (m, 1 H); 1.19-1.11 (m, 1 H); 0.85-0.77 (m, 2 H); 0.60 (t, J=7.3 Hz, 3 H). LC3 2.57 min (M+H) 343

Aufarbeitung

  1. concentrationThe solution was concentrated
  2. customthe nonvolatile portion was partitioned between aqueous 2N hydrochloric acid and EtOAc
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-5095a291f38148d5bf684417ebd960d8
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09012488B2

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