Sodium hydride → 6-((2R)-2-Hydroxy-4-(3-pyridyl)-1-butoxy)naphthalen-2-yloxyacetic acid methyl ester

HRID 1600964Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1600964
C1(C)C=CC(S([O:10][CH2:11][C@H:12]([O:21][Si](C(C)(C)C)(C)C)[CH2:13][CH2:14][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)(=O)=O)=CC=1.[CH3:30][O:31][C:32](=[O:46])[CH2:33][O:34][C:35]1[CH:44]=[CH:43][C:42]2[C:37](=[CH:38][CH:39]=[C:40](O)[CH:41]=2)[CH:36]=1.[H-].[Na+].O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CN(C)C=O.O1CCCC1.O>[CH3:30][O:31][C:32](=[O:46])[CH2:33][O:34][C:35]1[CH:44]=[CH:43][C:42]2[C:37](=[CH:38][CH:39]=[C:40]([O:10][CH2:11][C@H:12]([OH:21])[CH2:13][CH2:14][C:15]3[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=3)[CH:41]=2)[CH:36]=1

Komponenten

8

Edukt 4

HCID 24758Sodium hydrideHCID 162116731-Butanaminium, N,N,N-tributyl-, fluoride, hydrateHCID 54162583(2R)-2-(tert-butyldimethylsilyloxy)-4-(3-pyridyl)-1-butyl para-toluenesulfonateHCID 545394676-Hydroxy-2-naphthyloxyacetic acid methyl ester

Produkt 1

HCID 541642626-((2R)-2-Hydroxy-4-(3-pyridyl)-1-butoxy)naphthalen-2-yloxyacetic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

Prepared according to the method described in example 26e) from (2R)-2-(tert-butyldimethylsilyloxy)-4-(3-pyridyl)-1-butyl para-toluenesulfonate (1.00 g), 6-Hydroxy-2-naphthyloxyacetic acid methyl ester, sodium hydride (60% dispersion in mineral oil, 0.11 g) in dimethylformamide (15 ml) with heating at 75° C. for 1 hour. The adduct was dissolved in tetrahydrofuran (10 ml) and tetrabutylammonium fluoride hydrate (1.5 g) was added. After 4 hours, the mixture was diluted with water and extracted with ether. The organic extracts were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography over silica eluting with hexane:acetone (3:2 then 1:1) to give the sub-title compound as a solid (0.22 g).

Aufarbeitung

  1. customPrepared
  2. extractionextracted with ether
  3. dry with materialThe organic extracts were dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography over silica eluting with hexane:acetone (3:2

Quellen und Nachweise

ORD-Eintrag
ord-54f0025f35cf42e789bf0fc763336de0
Quelldatensatz
uspto-grants-1999_11
Patentnummer
US05977105

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