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Triphenylphosphine → Ethyl [2-methyl-4-({[4-{[3-(5-methyl-1,2,4-oxadiazol-3-yl)phenoxy]methyl}-2-(4-{trifluoromethyl}phenyl)-1,3-thiazol-5-yl]methyl}sulfanyl)phenoxy]acetate

HRID 270154
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 270154
[OH:1][CH2:2][C:3]1[N:4]=[C:5]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=2)[S:6][C:7]=1[CH2:8][S:9][C:10]1[CH:22]=[CH:21][C:13]([O:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:12]([CH3:23])[CH:11]=1.[CH3:34][C:35]1[O:39][N:38]=[C:37]([C:40]2[CH:41]=[C:42](O)[CH:43]=[CH:44][CH:45]=2)[N:36]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1(C)C=CC=CC=1>[CH3:23][C:12]1[CH:11]=[C:10]([S:9][CH2:8][C:7]2[S:6][C:5]([C:24]3[CH:25]=[CH:26][C:27]([C:30]([F:32])([F:33])[F:31])=[CH:28][CH:29]=3)=[N:4][C:3]=2[CH2:2][O:1][C:42]2[CH:43]=[CH:44][CH:45]=[C:40]([C:37]3[N:36]=[C:35]([CH3:34])[O:39][N:38]=3)[CH:41]=2)[CH:22]=[CH:21][C:13]=1[O:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 120425193-(5-Methyl-1,2,4-oxadiazol-3-yl)phenolHCID 86591789Ethyl [4-({[4-(hydroxymethyl)-2-(4-{trifluoromethyl}phenyl)-1,3-thiazol-5-yl]methyl}sulfanyl)-2-methylphenoxy]acetate

Produkt 1

HCID 86591788
Ethyl [2-methyl-4-({[4-{[3-(5-methyl-1,2,4-oxadiazol-3-yl)phenoxy]methyl}-2-(4-{trifluoromethyl}phenyl)-1,3-thiazol-5-yl]methyl}sulfanyl)phenoxy]acetate
Ausbeute 76,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a stirred solution of ethyl [4-({[4-(hydroxymethyl)-2-(4-{trifluoromethyl}phenyl)-1,3-thiazol-5-yl]methyl}sulfanyl)-2-methylphenoxy]acetate (40mg, 0.08mmoles, 1eq) in dry toluene (2ml) was added 3-(5-methyl-1,2,4-oxadiazol-3-yl)phenol (15mg, 0.088mmoles, 1.1eq) followed by triphenylphosphine (25mg, 0.096mmoles, 1.2eq) as a solid. Diisopropylazodicarboxylate (0.017ml, 0.088mmoles, 1.1eq) was then added dropwise and the reaction was stirred for 2hours at room temperature. The reaction was then partitioned between EtOAc and H2O. After the separation of the phases the organic phase washed with 0.1N NaOH, brine, dried over Na2SO4, filtered, concentrated in vacuo and purified via flash chromatography (10% EtOAc/Hexanes to 35% EtOAc/Hexanes) to yield 40mg (76%) of product.

Aufarbeitung

  1. customThe reaction was then partitioned between EtOAc and H2O
  2. customAfter the separation of the phases the organic phase
  3. washwashed with 0.1N NaOH, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. custompurified via flash chromatography (10% EtOAc/Hexanes to 35% EtOAc/Hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-3a08f893d6314f1dba3850155675d862
Quelldatensatz
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07449468B2

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