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Sodium hydride → Rac-3-{1-[2-(3,5-dimethoxy-phenyl)-5-methyl-oxazol-4-ylmethyl]-1h-indol-4-yl}-2-ethoxy-propionic acid ethyl ester

HRID 11382
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 11382
[H-].[Na+].[CH2:3]([O:5][C:6](=[O:21])[CH:7]([O:18][CH2:19][CH3:20])[CH2:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][NH:13]2)[CH3:4].Cl[CH2:23][C:24]1[N:25]=[C:26]([C:30]2[CH:35]=[C:34]([O:36][CH3:37])[CH:33]=[C:32]([O:38][CH3:39])[CH:31]=2)[O:27][C:28]=1[CH3:29]>CN(C)C=O.O>[CH2:3]([O:5][C:6](=[O:21])[CH:7]([O:18][CH2:19][CH3:20])[CH2:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][N:13]2[CH2:23][C:24]1[N:25]=[C:26]([C:30]2[CH:35]=[C:34]([O:36][CH3:37])[CH:33]=[C:32]([O:38][CH3:39])[CH:31]=2)[O:27][C:28]=1[CH3:29])[CH3:4]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 21974252Oxazole, 4-(chloromethyl)-2-(3,5-dimethoxyphenyl)-5-methyl-HCID 69279879Rac-2-ethoxy-3-(1h-indol-4-yl)-propionic acid ethyl ester

Produkt 1

HCID 69279866Rac-3-{1-[2-(3,5-dimethoxy-phenyl)-5-methyl-oxazol-4-ylmethyl]-1h-indol-4-yl}-2-ethoxy-propionic acid ethyl esterAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

0.048 g (1.10 mmol) Sodium hydride (55% in mineral oil) was added in one portion below 5° C. and under argon to a stirred solution of 0.261 g (1.00 mmol) rac-2-ethoxy-3-(1H-indol-4-yl)-propionic acid ethyl ester and 0.321 g (1.20 mmol) 4-chloromethyl-2-(3,5-dimethoxy-phenyl)-5-methyl-oxazole in 15.0 ml N,N-dimethylformamide. The reaction mixture was warmed up to room temperature and then stirred for 16 hours at ambient temperature. It was then diluted with cold water and extracted two times with ethyl acetate. The combined organic phases were dried over MgSO4, filtered and evaporated. The residue formed was purified by flash-chromatography (silica gel; eluent: gradient of hexane and ethyl acetate) to give 0.413 g (84%) rac-3-{1-[2-(3,5-dimethoxy-phenyl)-5-methyl-oxazol-4-ylmethyl]-1H-indol-4-yl}-2-ethoxy-propionic acid ethyl ester as light yellow solid.

Aufarbeitung

  1. extractionextracted two times with ethyl acetate
  2. dry with materialThe combined organic phases were dried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue formed
  6. customwas purified by flash-chromatography (silica gel; eluent: gradient of hexane and ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-2bbd1173503f43e4a80adb2b4bc005c0
Quelldatensatz
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07098228B2

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