1,2-Dichloroethane → 4-[2-[2-(4-Fluoro-phenyl)-ethylsulfanyl]-2-(2,2,2-trichloro-ethoxycarbonyl)-ethyl]-benzoic acid 2-phenyl-5-trifluoromethyl-oxazol-4-ylmethylester

HRID 709457노트

반응식

HRID 709457 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][S:10][CH:11]([C:22]([O:24][CH2:25][C:26]([Cl:29])([Cl:28])[Cl:27])=[O:23])[CH2:12][C:13]2[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.[C:30]1([C:36]2[O:37][C:38]([C:43]([F:46])([F:45])[F:44])=[C:39]([CH2:41]O)[N:40]=2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(Cl)CCl.Cl>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:30]1([C:36]2[O:37][C:38]([C:43]([F:46])([F:45])[F:44])=[C:39]([CH2:41][O:18][C:17](=[O:19])[C:16]3[CH:20]=[CH:21][C:13]([CH2:12][CH:11]([S:10][CH2:9][CH2:8][C:5]4[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=4)[C:22]([O:24][CH2:25][C:26]([Cl:29])([Cl:27])[Cl:28])=[O:23])=[CH:14][CH:15]=3)[N:40]=2)[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

참가 물질

7

반응물 4

HCID 111,2-DichloroethaneHCID 313Hydrochloric AcidHCID 58118959HCID 58118959, 화합물HCID 668648234-[2-[2-(4-Fluoro-phenyl)-ethylsulfanyl]-2-(2,2,2-trichloro-ethoxycarbonyl)-ethyl]-benzoic acid

생성물 1

HCID 866503034-[2-[2-(4-Fluoro-phenyl)-ethylsulfanyl]-2-(2,2,2-trichloro-ethoxycarbonyl)-ethyl]-benzoic acid 2-phenyl-5-trifluoromethyl-oxazol-4-ylmethylester수율 70.7%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

To a solution of 4-[2-[2-(4-fluoro-phenyl)-ethylsulfanyl]-2-(2,2,2-trichloro-ethoxy-carbonyl)-ethyl]-benzoic acid (278 mg, 0.58 mmol) and (2-phenyl-5-trifluoromethyl-oxazol-4-yl)-methanol (155 mg, 0.64 mmol) in anhydrous DCM (20 mL) was first added EDC×HCl (144 mg, 0.75 mmol) then DMAP (1.0 mg, 0.006 mol) under nitrogen atmosphere at 0° C. After complete addition the cooling bath was removed and the reaction mixture was stirred at ambient temperature until no starting material was left. The mixture was diluted with water and aq. HCl (2N) and extracted with DCM. The combined organic layers were dried (MgSO4) and the solvent was evaporated under reduced pressure. The crude product was purified by flash chromatography using n-heptane/EtOAc 4:1 as the eluent to afford the final product as an oil (289 mg, 56.6%). 1H NMR (400 MHz, CDCl3): δ 8.02 (d, 2H), 7.93 (d, 1H), 7.40-7.47 (m, 2H), 7.19-7.29 (m, 4H), 7.02 (dt, 2H), 6.89 (dt, 2H), 5.34 (d, 2H), 4.64 (q, 2H), 3.50 (dd, 1H), 3.18-3.24 (dd, 1H), 2.73-2.98 (m, 5H), 1.1 (s, 2H). Mass Spectrum: M−H+ 703.91.

후처리

  1. customat 0° C
  2. additionAfter complete addition the cooling bath
  3. customwas removed
  4. waitwas left
  5. additionThe mixture was diluted with water and aq. HCl (2N)
  6. extractionextracted with DCM
  7. dry with materialThe combined organic layers were dried (MgSO4)
  8. customthe solvent was evaporated under reduced pressure
  9. customThe crude product was purified by flash chromatography

출처 및 근거

ORD 기록
ord-dc40508c81844ea29feb5da3a2365c8b
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181181B2

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