반응 #45370

반응 방정식

Oxalyl chloride

title compound

2′-{[[3,5-Bis(trifluoromethyl)benzyl](methoxycarbonyl)amino]methyl}-6-methoxy-4′-(trifluoromethyl)biphenyl-3-carboxylic acid

acetamide oxime

→

title compound

Methyl [3,5-bis(trifluoromethyl)benzyl]{[2′-methoxy-5′-(3-methyl-1,2,4-oxadiazol-5-yl)-4-(trifluoromethyl)biphenyl-2-yl]methyl}carbamate

용매

methylene chloride

반응 조건

후처리

1. 1
   농축then concentrated in vacuo
2. 2
   workup.DISSOLUTIONThe crude product was re-dissolved in anhydrous dichloroethane
3. 3
   온도to increase solubility
4. 4
   온도The reaction was heated to and
5. 5
   온도maintained
6. 6
   온도at reflux overnight
7. 7
   온도Once the reaction cooled to room temperature
8. 8
   기타the solvent was removed through evaporation
9. 9
   세척washed with water
10. 10
    건조brine, dried over anhydrous sodium sulfate
11. 11
    여과filtered
12. 12
    농축concentrated

실험 절차

Oxalyl chloride (0.14 mL, 0.28 mmol) and a few drops of dimethylformamide were added to a solution of the title compound from Example 145 (86 mg, 0.14 mmol) in methylene chloride. The reaction mixture was stirred at room temperature for 1 h then concentrated in vacuo. The crude product was re-dissolved in anhydrous dichloroethane, and acetamide oxime (16 mg, 0.21 mmol) was added along with a few drops of dimethylformamide to increase solubility. The reaction was heated to and maintained at reflux overnight. Once the reaction cooled to room temperature, the solvent was removed through evaporation. The oil was taken up in methylene chloride, washed with water, then brine, dried over anhydrous sodium sulfate, filtered and concentrated. The title compound was obtained by preparative thin layer chromatography using 50% EtOAc/hexane. 1H NMR (CDCl3, 600 MHz) δ 8.15 (s, 1H), 7.86 (s, 1H), 7.71 (s, 1H), 7.62 (d, J=8.4 Hz, 1H), 7.43-7.56 (m, 3H), 7.35 (d, J=7.8 Hz, 1H), 7.07 (m, 1H), 4.20-4.60 (m, 4H), 3.81 (s, 3H), 3.70 (m, 3H), 2.46 (s, 3H). LC-MS (M+1) 647.9 (4.40 min).

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