Trifluoromethanesulfonic acid → HCID 178502735、化合物

HRID 1036535ノート

反応式

HRID 1036535 の反応式
[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

参加物

5

反応物 3

HCID 62406Trifluoromethanesulfonic acidHCID 144968Benzyl 2,2,2-trichloroacetimidateHCID 178502733HCID 178502733、化合物

生成物 1

HCID 178502735HCID 178502735、化合物収率 96.4%

試薬・触媒・溶媒 1

HCID 21916607Dichloromethane cyclohexane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-3693e2b52a184e8cbe0716ad0371d646
出典データセット
uspto-grants-2013_10
特許番号
US08546359B2

反応ノート

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