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Water → 2-Methyl-2-{[4-(2-oxo-2-{[4'-(trifluoromethyl)biphenyl-4-yl]amino}ethyl)-1,3-thiazol-2-yl]thio}propionic acid tert-butyl ester

HRID 914385
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 914385
[C:1]([O:5][C:6](=[O:27])[C:7]([S:10][C:11]1[S:12][CH:13]=[C:14]([CH2:16][C:17]([NH:19][C:20]2[CH:25]=[CH:24][C:23](Br)=[CH:22][CH:21]=2)=[O:18])[N:15]=1)([CH3:9])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[F:28][C:29]([F:41])([F:40])[C:30]1[CH:35]=[CH:34][C:33](OB(O)O)=[CH:32][CH:31]=1.O>O1CCOCC1.C(=O)([O-])[O-].[Na+].[Na+].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([O:5][C:6](=[O:27])[C:7]([CH3:9])([S:10][C:11]1[S:12][CH:13]=[C:14]([CH2:16][C:17](=[O:18])[NH:19][C:20]2[CH:25]=[CH:24][C:23]([C:33]3[CH:34]=[CH:35][C:30]([C:29]([F:41])([F:40])[F:28])=[CH:31][CH:32]=3)=[CH:22][CH:21]=2)[N:15]=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2]
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Komponenten

7

Edukt 3

HCID 962WaterHCID 17793420p-Trifluoromethylphenylboric acidHCID 673959082-[(4-{2-[(4-Bromophenyl)amino]-2-oxoethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl ester

Produkt 1

HCID 597589402-Methyl-2-{[4-(2-oxo-2-{[4'-(trifluoromethyl)biphenyl-4-yl]amino}ethyl)-1,3-thiazol-2-yl]thio}propionic acid tert-butyl esterAusbeute 80,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysator
HCID 10340Sodium CarbonateLösungsmittel
HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Under nitrogen atmosphere, 2-[(4-{2-[(4-bromophenyl)amino]-2-oxoethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl ester (600 mg) synthesized in Example 458-1 and 4-trifluoromethylphenylboric acid (363 mg) were dissolved in dioxane (8 mL) and 2M aqueous sodium carbonate solution (4 mL), tetrakis(triphenylphosphine)palladium (73 mg) was added, and the mixture was refluxed for 4 hr. The reaction mixture was cooled, water was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=2:1) to give the title compound (550 mg) as a colorless oil.

Aufarbeitung

  1. temperaturethe mixture was refluxed for 4 hr
  2. temperatureThe reaction mixture was cooled
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=2:1)

Quellen und Nachweise

ORD-Eintrag
ord-30b1b971103e4cfd9e26c6b34f24c5e8
Quelldatensatz
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08026370B2

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