Lithium hydroxide, monohydrate → HCID 44546375, Verbindung

HRID 1094367Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1094367
[CH3:1][C:2]1[CH:3]=[C:4]([N:9]([CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][N:26]=2)[C:10]([C@@H:12]([O:19]C(=O)C)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:11])[CH:5]=[CH:6][C:7]=1[CH3:8].O.[OH-].[Li+]>O1CCCC1.O>[CH3:1][C:2]1[CH:3]=[C:4]([N:9]([CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:33])([F:34])[F:32])=[CH:27][N:26]=2)[C:10](=[O:11])[C@@H:12]([OH:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:5]=[CH:6][C:7]=1[CH3:8]

Komponenten

5

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 44546441HCID 44546441, Verbindung

Produkt 1

HCID 44546375HCID 44546375, VerbindungAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 116 mg (0.25 mmol) acetic acid (S)-{(3,4-dimethyl-phenyl)-[2-(5-trifluoromethyl-pyridin-2-yl)-ethyl]-carbamoyl}-phenyl-methyl ester in 1.2 mL tetrahydrofuran were added 0.6 mL water and 11.4 mg (0.27 mmol) lithium hydroxide monohydrate. The mixture was stirred at room temperature overnight. The mixture was diluted with water and extracted 3 times with ethyl acetate. The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. The crude oil was purified with flash column chromatography on silica eluting with a gradient formed from heptane and ethylacetate to provide 0.098 g (93%) of the title compound as a colorless oil. MS(m/e): 429.2 [M+H]+.

Aufarbeitung

  1. extractionextracted 3 times with ethyl acetate
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude oil was purified with flash column chromatography on silica eluting with a gradient
  6. customformed from heptane and ethylacetate

Quellen und Nachweise

ORD-Eintrag
ord-9e84607c5afe4ca7a014fa60dc391a19
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08133909B2

Notizen zur Reaktion

Wird geladen…