Trifluoromethanesulfonic acid → HCID 178502735, 화합물

HRID 1036535노트

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HRID 1036535 반응식
[OH:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]([N:10]([O:12][CH3:13])[CH3:11])=[O:9])[CH2:4][CH2:3]1.[CH2:14](OC(=N)C(Cl)(Cl)Cl)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.FC(F)(F)S(O)(=O)=O>C1CCCCC1.C(Cl)Cl>[CH2:14]([O:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]([N:10]([O:12][CH3:13])[CH3:11])=[O:9])[CH2:4][CH2:3]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

참가 물질

5

반응물 3

HCID 62406Trifluoromethanesulfonic acidHCID 144968Benzyl 2,2,2-trichloroacetimidateHCID 178502733HCID 178502733, 화합물

생성물 1

HCID 178502735HCID 178502735, 화합물수율 96.4%

시약·촉매·용매 1

HCID 21916607Dichloromethane cyclohexane용매

실험 절차

To a mixture of cis-4-hydroxy-N-methoxy-N-methylcyclohexanecarboxamide (3.556 g, 0.0190 mol) and benzyl-2,2,2-trichloroacetimidate (4.0 mL, 0.021 mol, 1.1 eq) in cyclohexane/DCM (20 mL/10 mL) at 0° C. was added trifluoromethanesulfonic acid dropwise with stirring under nitrogen atmosphere over 30 min. There was an immediate precipitate. The mixture was stirred at room temperature for 15 h, filtered, and the filtrate washed with sodium bicarbonate solution and brine. The organic layer was concentrated and purified by silica gel column chromatography using petroleum ether/ethyl acetate (5/1) as eluent to give product as a colorless oil (5.079 g, 77%). 1H NMR (400 MHz, CDCl3) δ7.38-7.23 (m, 5H), 4.50 (s, 2H), 3.71 (s, 3H), 3.70-3.66 (m, 1H), 3.18 (s, 3H), 2.78-2.62 (m, 1H), 2.07-1.89 (m, 4H), 1.59-1.25 (m, 4H).

후처리

  1. stirringThe mixture was stirred at room temperature for 15 h
  2. filtrationfiltered
  3. washthe filtrate washed with sodium bicarbonate solution and brine
  4. concentrationThe organic layer was concentrated
  5. custompurified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-3693e2b52a184e8cbe0716ad0371d646
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546359B2

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