Water → tert-Butyl 4-(5-methyl-1,2,4-oxadiazol-3-yl)piperazine-1-carboxylate

HRID 1775320ノート

反応式

HRID 1775320 の反応式
[OH:1][NH:2][C:3]([N:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1)=[NH:4].[C:18](OC(=O)C)(=O)[CH3:19].O>N1C=CC=CC=1>[CH3:18][C:19]1[O:1][N:2]=[C:3]([N:5]2[CH2:6][CH2:7][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:9][CH2:10]2)[N:4]=1

参加物

5

反応物 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 178452346tert-butyl 4-(N-hydroxyamidino)-piperazine-1-carboxylate

生成物 1

HCID 86686046tert-Butyl 4-(5-methyl-1,2,4-oxadiazol-3-yl)piperazine-1-carboxylate収率 91.3%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
80 °C

実験手順

To a solution of tert-butyl 4-(N-hydroxycarbamimidoyl)piperazine-1-carboxylate (771 mg, 3.16 mmol) in pyridine (8 mL) was added acetic anhydride (320 L, 3.42 mmol) and the reaction was heated to 80° C. for 3 h. The mixture was cooled to room temperature, poured into water and extracted with EtOAc. The organic layer was washed with water and brine, dried (Na2SO4) and concentrated under reduced pressure to yield 774 mg of a yellow solid. After purification by flash chromatography (silica, gradient of 0.5 to 3% methanol in dichloromethane) 509 mg of an off-white solid were obtained (1.897 mmol, 60%). MS (ESI) m/z=291.1 [M+Na]+.

後処理

  1. temperatureThe mixture was cooled to room temperature
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-c4381c964faf4a398db4a678fee17190
出典データセット
uspto-grants-2016_02
特許番号
US09260441B2

反応ノート

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