Triethylammonium hydroxide → HCID 89852256、化合物

HRID 627087ノート

反応式

HRID 627087 の反応式
[CH2:1]([O:4][N:5]1[C:11](=[O:12])[N:10]2[CH2:13][C@H:6]1[C:7]([CH3:17])=[CH:8][C@H:9]2[C:14]([NH2:16])=O)[CH:2]=[CH2:3].[OH-].C([NH+](CC)CC)C>C(Cl)Cl>[CH2:1]([O:4][N:5]1[C:11](=[O:12])[N:10]2[CH2:13][C@H:6]1[C:7]([CH3:17])=[CH:8][C@H:9]2[C:14]#[N:16])[CH:2]=[CH2:3]

参加物

4

反応物 2

HCID 21903323Triethylammonium hydroxideHCID 89851371HCID 89851371、化合物2 回

生成物 1

HCID 89852256HCID 89852256、化合物収率 83%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of (2S,5R)-6-(allyloxy)-4-methyl-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-ene-2-carboxamide (Intermediate 16, 146 mg, 0.62 mmol) in DCM (6 mL), under nitrogen, at room temperature was added methoxycarbonylsulfamoyl)triethyl-ammonium hydroxide inner salt (Burgess Reagent) (660 mg, 2.77 mmol) portionwise over 2 hours. The reaction was stirred at room temperature for an additional 30 minutes. The reaction mixture was washed with 1:1 brine:water. The organic layer was dried over magnesium sulfate, filtered and concentrated. Silica gel chromatography (0%-25% ethyl acetate/hexanes) afforded (2S,5R)-6-(allyloxy)-4-methyl-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-ene-2-carbonitrile (112 mg, 83%) as a colorless oil.

後処理

  1. washThe reaction mixture was washed with 1:1 brine
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-329d1bd7253643d8b621717b5096376a
出典データセット
uspto-grants-2016_04
特許番号
US09309245B2

反応ノート

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