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

HRID 1628184Notes

Reaction equation

HRID 1628184 reaction equation
[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

Participants

5

Reactant 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

Product 1

HCID 668653674-{2-Carboxy-2-[2-(4-fluoro-phenyl)-ethylsulfanyl]-ethyl}-benzoic acid 2-phenyl-5 trifluoromethyl-oxazol-4-ylmethyl esterYield 10.2%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-e9e58ac300be4d61be239dde8d0f0548
Source dataset
uspto-grants-2014_07
Patent number
US08785681B2

Reaction notes

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