Pyridine, hydrofluoride (1:1) → HCID 68815279、化合物

HRID 732555ノート

反応式

HRID 732555 の反応式
[F:1][B-](F)(F)F.N#[O+].[CH3:8][O:9][C:10](=[O:34])[C:11]1[CH:23]=[C:22]([C:24]2([C:29]3[O:30][CH:31]=[CH:32][CH:33]=3)SCCS2)[CH:21]=[C:13]([C:14]([N:16]([CH3:20])[CH2:17][CH2:18][CH3:19])=[O:15])[CH:12]=1.C1C=CN=CC=1.[FH:41]>ClCCl>[CH3:8][O:9][C:10](=[O:34])[C:11]1[CH:23]=[C:22]([C:24]([F:1])([F:41])[C:29]2[O:30][CH:31]=[CH:32][CH:33]=2)[CH:21]=[C:13]([C:14]([N:16]([CH3:20])[CH2:17][CH2:18][CH3:19])=[O:15])[CH:12]=1

参加物

5

反応物 3

HCID 64774Pyridine, hydrofluoride (1:1)HCID 11137142Nitrilooxonium tetrafluoroborateHCID 86615015HCID 86615015、化合物

生成物 1

HCID 68815279HCID 68815279、化合物収率 30%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

反応条件

温度
0 °C

実験手順

Under nitrogen and in a plastic vessel, dissolve nitrosonium tetrafluoroborate (84.8 μg, 0.72 mmol) and pyridinium poly(hydrogen fluoride) (70% hydrogen fluoride, 30% pyridine, 300 μL) in dichloromethane (2 mL) and cool to 0° C. Add dropwise 5-(2-furan-2-yl-[1,3]dithiolan-2-yl)-N-methyl-N-propyl-isophthalamic acid methyl ester in dichloromethane (1.5 mL) to the mixture, warm up to room temperature and stir for 2 h. Dilute the mixture with dichloromethane (20 mL) and filter the organic liquid though a pad of aluminum oxide and magnesium sulfate mixture. Concentrate the filtrate and purify (silica gel chromatography, 1:99 to 30:70 ethyl acetate:hexanes) to give the title compound (30%).

後処理

  1. temperaturewarm up to room temperature
  2. filtrationfilter the organic liquid though a pad of aluminum oxide and magnesium sulfate mixture
  3. concentrationConcentrate the filtrate
  4. custompurify (silica gel chromatography, 1:99 to 30:70 ethyl acetate:hexanes)

出典と根拠

ORDレコード
ord-1e20638298a14eda8f2ac03579660884
出典データセット
uspto-grants-2009_09
特許番号
US07585885B2

反応ノート

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