Ammonium Chloride → HCID 67029513、化合物

HRID 1465447ノート

反応式

HRID 1465447 の反応式
[Cl-].[C:2]([O:6][C:7]([NH:9][NH:10][C:11]([CH2:13][C:14]1[CH:39]=[CH:38][C:17]([CH2:18][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:16][CH:15]=1)=[O:12])=[O:8])([CH3:5])([CH3:4])[CH3:3].C([Li])CCC.[CH:45]([C:47]1[S:51][C:50]([NH:52][C:53](=[O:55])[CH3:54])=[CH:49][CH:48]=1)=O.[Cl-].[NH4+]>O1CCCC1>[C:53]([NH:52][C:50]1[S:51][C:47]([CH:45]=[CH:18][C:17]2[CH:16]=[CH:15][C:14]([CH2:13][C:11]([NH:10][NH:9][C:7]([O:6][C:2]([CH3:3])([CH3:4])[CH3:5])=[O:8])=[O:12])=[CH:39][CH:38]=2)=[CH:48][CH:49]=1)(=[O:55])[CH3:54]

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 268899N-(5-Formyl-2-thienyl)acetamideHCID 86651838HCID 86651838、化合物HCID 178418339Butyllithium

生成物 1

HCID 67029513HCID 67029513、化合物収率 28%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

{4-[2-(tert-Butoxycarbonyl)hydrazinocarbonylmethyl]benzyl}(triphenyl)phosphonium chloride (2.97 g, 5.29 mmol) was suspended in anhydrous tetrahydrofuran (8 ml), and cooled to −78° C. n-Butyllithium (1.6M-hexane solution, 3.3 ml, 5.3 mmol) was added dropwise, and the mixture was stirred at −78° C. for 15 mins and at 0° C. for 2 hrs. A solution of N-(5-formylthiophen-2-yl)acetamide (280 mg, 1.65 mmol) in anhydrous tetrahydrofuran (2 ml) was added dropwise, and the mixture was warmed to room temperature. After stirring at room temperature overnight, saturated aqueous ammonium chloride solution was added. The mixture was extracted with dichloromethane and the combined organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate and concentrated. The residue was purified by silica gel column chromatography (dichloromethane:methanol=97:3→80:20) to give tert-butyl 2-({4-[2-(5-acetylaminothiophen-2-yl)vinyl]phenyl}acetyl)hydrazinecarboxylate (192 mg, yield 28%, E/Z mixture) as a yellow solid.

後処理

  1. additionwas added dropwise
  2. temperaturethe mixture was warmed to room temperature
  3. stirringAfter stirring at room temperature overnight
  4. extractionThe mixture was extracted with dichloromethane
  5. washthe combined organic layer was washed with water and saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column chromatography (dichloromethane:methanol=97:3→80:20)

出典と根拠

ORDレコード
ord-774ebe64261c4fa0b72d0bc9e2d0b9f1
出典データセット
uspto-grants-2015_04
特許番号
US08999989B2

反応ノート

読み込み中…