Triethylamine → [5-(4-Bromo-3-methyl-phenyl)-3-methyl-isoxazol-4-yl]carbamic acid (R)-1-(2-fluoro-phenyl)-ethyl Ester

HRID 2092440Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2092440
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[C:9]=2C(O)=O)=[CH:4][C:3]=1[CH3:17].C([N:20]([CH2:23]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:32])C=CC=CC=1.[F:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=1[C@H:49]([OH:51])[CH3:50]>C1(C)C=CC=CC=1>[F:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=1[C@H:49]([O:51][C:23](=[O:32])[NH:20][C:9]1[C:10]([CH3:13])=[N:11][O:12][C:8]=1[C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[C:3]([CH3:17])[CH:4]=1)[CH3:50]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 2779054(R)-1-(2-Fluorophenyl)ethanolHCID 585394455-(4-Bromo-3-methyl-phenyl)-3-methyl-isoxazole-4-carboxylic acid

Produkt 1

HCID 54765945[5-(4-Bromo-3-methyl-phenyl)-3-methyl-isoxazol-4-yl]carbamic acid (R)-1-(2-fluoro-phenyl)-ethyl Ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

5-(4-Bromo-3-methyl-phenyl)-3-methyl-isoxazole-4-carboxylic acid (1.78 g, 6.0 mmol) was dissolved in toluene (50 mL). Triethylamine (0.92 mL, 6.6 mmol) was added, followed by diphenylphosphoryl azide (1.43 mL, 6.6 mmol), and the mixture was stirred for 10 minutes. (R)-1-(2-Fluoro-phenyl)-ethanol (0.924 g, 6.6 mmol) was added, and the reaction was stirred at 85° C. for 3 hours, and then overnight at room temperature. The mixture was concentrated, and the residue was diluted with dichloromethane and purified by silica gel chromatography to give the title compound.

Aufarbeitung

  1. stirringthe reaction was stirred at 85° C. for 3 hours
  2. customovernight
  3. customat room temperature
  4. concentrationThe mixture was concentrated
  5. additionthe residue was diluted with dichloromethane
  6. custompurified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-f9856a0c813e4a3c9e8b2b9c62c56303
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08440707B2

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