Trifluoroacetic anhydride → 5-(3,5-dichloro-phenyl)-3-[4-(1H-pyrazol-4-yl)-naphthalen-1-yl]-5-trifluoromethyl-4,5-dihydro-isoxazole

HRID 388371Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 388371
FC(F)(F)C(OC(=O)C(F)(F)F)=O.C(OC([N:21]1[CH:25]=[C:24]([C:26]2[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:29]([C:36]3[CH2:40][C:39]([C:45]4[CH:50]=[C:49]([Cl:51])[CH:48]=[C:47]([Cl:52])[CH:46]=4)([C:41]([F:44])([F:43])[F:42])[O:38][N:37]=3)=[CH:28][CH:27]=2)[CH:23]=[N:22]1)=O)(C)(C)C.[OH-].[Na+]>ClCCl>[Cl:51][C:49]1[CH:50]=[C:45]([C:39]2([C:41]([F:43])([F:42])[F:44])[O:38][N:37]=[C:36]([C:29]3[C:30]4[C:35](=[CH:34][CH:33]=[CH:32][CH:31]=4)[C:26]([C:24]4[CH:23]=[N:22][NH:21][CH:25]=4)=[CH:27][CH:28]=3)[CH2:40]2)[CH:46]=[C:47]([Cl:52])[CH:48]=1

Komponenten

5

Edukt 3

HCID 9845Trifluoroacetic anhydrideHCID 14798Sodium HydroxideHCID 674362084-{4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-naphthalen-1-yl}-pyrazole-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 468423985-(3,5-dichloro-phenyl)-3-[4-(1H-pyrazol-4-yl)-naphthalen-1-yl]-5-trifluoromethyl-4,5-dihydro-isoxazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Trifluoroacetic acid anhydride (0.18 ml) is added to a solution of 4-{4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-naphthalen-1-yl}-pyrazole-1-carboxylic acid tert-butyl ester (135 mg) in dichloromethane (1 ml). After 1 hour at room temperature an aqueous solution of sodium hydroxide (30%) is added. The aqueous phase is extracted with dichloromethane and the combined organic phases are dried over MgSO4 and concentrated in vacuo. The crude product is purified on a semi-preparative HPLC to yield 5-(3,5-dichloro-phenyl)-3-[4-(1H-pyrazol-4-yl)-naphthalen-1-yl]-5-trifluoromethyl-4,5-dihydro-isoxazole as a colorless solid: m.p. 117-120° C. (compound 1.17, table 1).

Aufarbeitung

  1. extractionThe aqueous phase is extracted with dichloromethane
  2. dry with materialthe combined organic phases are dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe crude product is purified on a semi-preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-52533b5a58f746f1b3004fb65bc8ec0d
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08377942B2

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