Acetic Acid → 4-{2-Carboxy-2-[2-(4-fluoro-phenyl)-ethylsulfanyl]-ethyl}-benzoic acid 2-phenyl-5 trifluoromethyl-oxazol-4-ylmethyl ester

HRID 709499Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 709499
[C:1]1([C:7]2[O:8][C:9]([C:42]([F:45])([F:44])[F:43])=[C:10]([CH2:12][O:13][C:14](=[O:41])[C:15]3[CH:20]=[CH:19][C:18]([CH2:21][CH:22]([S:31][CH2:32][CH2:33][C:34]4[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=4)[C:23]([O:25]CC(Cl)(Cl)Cl)=[O:24])=[CH:17][CH:16]=3)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(=O)C>C(Cl)Cl.[Zn]>[C:1]1([C:7]2[O:8][C:9]([C:42]([F:43])([F:45])[F:44])=[C:10]([CH2:12][O:13][C:14](=[O:41])[C:15]3[CH:16]=[CH:17][C:18]([CH2:21][CH:22]([C:23]([OH:25])=[O:24])[S:31][CH2:32][CH2:33][C:34]4[CH:35]=[CH:36][C:37]([F:40])=[CH:38][CH:39]=4)=[CH:19][CH:20]=3)[N:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

5

Edukt 2

HCID 176Acetic AcidHCID 866503034-[2-[2-(4-Fluoro-phenyl)-ethylsulfanyl]-2-(2,2,2-trichloro-ethoxycarbonyl)-ethyl]-benzoic acid 2-phenyl-5-trifluoromethyl-oxazol-4-ylmethylester

Produkt 1

HCID 668653674-{2-Carboxy-2-[2-(4-fluoro-phenyl)-ethylsulfanyl]-ethyl}-benzoic acid 2-phenyl-5 trifluoromethyl-oxazol-4-ylmethyl esterAusbeute 10,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

4-[2-[2-(4-Fluoro-phenyl)-ethylsulfanyl]-2-(2,2,2-trichloro-ethoxycarbonyl)-ethyl]-benzoic acid 2-phenyl-5-trifluoromethyl-oxazol-4-ylmethylester (289 mg, 0.41 mmol) was dissolved in DCM (30 mL) and zinc (530 mg, 8.1 mmol) was added followed by acetic acid (2.5 mL, 41.6 mmol). The resulting suspension was stirred for 6 h at ambient temperature. After filtering off and washing the zinc with MeOH and EtOAc, the combined organic layers were extracted with water, dried (MgSO4) and evaporated under reduced pressure. The remaining crude product was purified by flash chromatography using Et2O/DCM/EtOAc 6:3:1 as the eluent to afford the title compound as a solid (yield: 24 mg, 10%). 1H NMR (400 MHz, CDCl3): δ 8.07 (d, 2H), 7.98 (d, 2H), 7.43-7.55 (m, 3H), 7.24 (d, 2H), 7.07 (m, 2H), 6.92 (t, 2H), 5.39 (s, 2H), 3.43 (t, 1H), 3.22 (dd, 1H), 2.75-2.99 (m, 5H). Mass spectrum: M+H+ 574.14, M−H+ 572.24.

Aufarbeitung

  1. filtrationAfter filtering off
  2. washwashing the zinc with MeOH and EtOAc
  3. extractionthe combined organic layers were extracted with water
  4. dry with materialdried (MgSO4)
  5. customevaporated under reduced pressure
  6. customThe remaining crude product was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-717cda36d5564b389d31e36bf6ade2d1
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181181B2

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