Phosphorus oxychloride → (S)-1-(4-Chloro-phenyl)-azetidine-2-carboxylic acid (5-tert-butyl-isoxazol-3-yl)-amide

HRID 389864Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 389864
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:11][CH2:10][C@H:9]2[C:12]([OH:14])=O)=[CH:4][CH:3]=1.[NH2:15][C:16]1[CH:20]=[C:19]([C:21]([CH3:24])([CH3:23])[CH3:22])[O:18][N:17]=1.P(Cl)(Cl)(Cl)=O>N1C=CC=CC=1.C(OCC)(=O)C>[C:21]([C:19]1[O:18][N:17]=[C:16]([NH:15][C:12]([C@@H:9]2[CH2:10][CH2:11][N:8]2[C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)=[O:14])[CH:20]=1)([CH3:24])([CH3:23])[CH3:22]

Komponenten

6

Edukt 3

HCID 24813Phosphorus oxychlorideHCID 1714733-Isoxazolamine, 5-(1,1-dimethylethyl)-HCID 67284015(S)-1-(4-Chloro-phenyl)-azetidine-2-carboxylic acid

Produkt 1

HCID 49847935(S)-1-(4-Chloro-phenyl)-azetidine-2-carboxylic acid (5-tert-butyl-isoxazol-3-yl)-amide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a cold solution (0° C.) of (S)-1-(4-Chloro-phenyl)-azetidine-2-carboxylic acid (100 mg; 0.472 mmol) and 3-amino-5-t-butylisoxazole (66 mg; 0.472 mmol) in pyridine (1.5 mL) is added phosphorus oxychloride (0.043 m; 0.48 mmol). The reaction mixture is stirred at room temperature for 18 hours. After this time, the reaction mixture is diluted with ethyl acetate and washed with diluted NH4Cl aqueous solution then brine, dried over Na2SO4, filtered and concentrated in vacuo. Purification by flash chromatography on silica gel using ethyl acetate/hexanes provides the title compound, m/z 334 [M+H+].

Aufarbeitung

  1. washwashed with diluted NH4Cl aqueous solution
  2. dry with materialbrine, dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification by flash chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-b2cc651ec39947a2ba3eca88ae25c82e
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08383615B2

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