Sodium hydride → HCID 67397409、化合物

HRID 1426744ノート

反応式

HRID 1426744 の反応式
[H-].[Na+].C1OCCOCCOCCOCCOC1.[F:18][C:19]1[C:20]([CH2:31][N:32]([CH3:40])[C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[CH:21][NH:22][C:23]=1[C:24]1[C:25]([F:30])=[N:26][CH:27]=[CH:28][CH:29]=1.[CH3:41][C:42]1[O:43][CH:44]=[CH:45][C:46]=1[S:47](Cl)(=[O:49])=[O:48]>O1CCCC1.O>[F:18][C:19]1[C:20]([CH2:31][N:32]([CH3:40])[C:33](=[O:39])[O:34][C:35]([CH3:36])([CH3:37])[CH3:38])=[CH:21][N:22]([S:47]([C:46]2[CH:45]=[CH:44][O:43][C:42]=2[CH3:41])(=[O:49])=[O:48])[C:23]=1[C:24]1[C:25]([F:30])=[N:26][CH:27]=[CH:28][CH:29]=1

参加物

7

反応物 4

HCID 24758Sodium hydrideHCID 3633615-Crown-5HCID 552797002-Methylfuran-3-sulfonyl chlorideHCID 67176761tert-butyl {[4-fluoro-5-(2-fluoropyridin-3-yl)-1H-pyrrol-3-yl]methyl}methylcarbamate

生成物 1

HCID 67397409HCID 67397409、化合物収率 61.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a suspension of sodium hydride (60% in oil, 34 mg) in tetrahydrofuran (4 mL) were added dropwise 15-crown-5 (0.17 mL), a solution of tert-butyl {[4-fluoro-5-(2-fluoropyridin-3-yl)-1H-pyrrol-3-yl]methyl}methylcarbamate (210 mg) in tetrahydrofuran (1 mL) and 2-methylfuran-3-sulfonyl chloride (176 mg) under ice-cooling, and the mixture was stirred for 0.5 hr. The reaction mixture was diluted with water, and extracted with ethyl acetate. The separated aqueous layer was extracted again with ethyl acetate. The combined organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=9:1→2:3) and basic silica gel column chromatography (eluent: hexane-ethyl acetate=17:3→1:1) to give the title compound as a pale-yellow oil (yield 187 mg, 61%).

後処理

  1. extractionextracted with ethyl acetate
  2. extractionThe separated aqueous layer was extracted again with ethyl acetate
  3. washThe combined organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=9:1→2:3) and basic silica gel column chromatography (eluent: hexane-ethyl acetate=17:3→1:1)

出典と根拠

ORDレコード
ord-6b2cba524c38418a89584c0b87aca3c4
出典データセット
uspto-grants-2015_01
特許番号
US08933105B2

反応ノート

読み込み中…