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

HRID 709499노트

반응식

HRID 709499 반응식
[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

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-717cda36d5564b389d31e36bf6ade2d1
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181181B2

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