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Sodium Hydroxide → Tert-butyl 4-[4-(4-amino-1,2,5-oxadiazol-3-yl)phenyl]piperazine-1-carboxylate

HRID 1744121
ノート
印刷プレビュー

反応式

HRID 1744121 の反応式
[C:1](/[C:3](=[N:23]\[OH:24])/[C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)#[N:2].Cl.[NH2:26]O.C([O-])(O)=O.[Na+].[OH-].[Na+]>CCO.O.[Cl-].[Na+].O>[NH2:2][C:1]1[C:3]([C:4]2[CH:5]=[CH:6][C:7]([N:10]3[CH2:11][CH2:12][N:13]([C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[CH2:14][CH2:15]3)=[CH:8][CH:9]=2)=[N:23][O:24][N:26]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 14798Sodium Hydroxide2 回HCID 443297Hydroxyamine hydrochloride2 回HCID 516892Sodium Bicarbonate2 回HCID 22236172tert-butyl 4-[4-[(Z)-C-cyano-N-hydroxycarbonimidoyl]phenyl]piperazine-1-carboxylate

生成物 1

HCID 22235822Tert-butyl 4-[4-(4-amino-1,2,5-oxadiazol-3-yl)phenyl]piperazine-1-carboxylate

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 962Water溶媒2 回HCID 57417360Sodium chloride; water溶媒

実験手順

To tert-butyl 4-{4-[(Z)-cyano(hydroxyimino)methyl]phenyl}piperazine-1-carboxylate (1.39 g, 4.21 mmol) in EtOH (50 mL) was added an aqueous solution of pre-mixed hydroxylamine hydrochloride (440 mg, 6.32 mmol) and NaHCO3 (535 mg, 6.32 mmol) in water (15 mL) and the reaction was refluxed overnight. An additional aliquot of hydroxylamine hydrochloride (440 mg, 6.32 mmol) and NaHCO3 (535 mg, 6.32 mmol) in water (10 mL) was added and the reaction was refluxed for 2 hours. Aqueous NaOH (1.0 M, 42.1 mL) was added and the reaction was refluxed for 1 hour. An additional aliquot of NaOH (1.0 M, 21 mL) was added and the reaction was refluxed for 3 hours. After cooling to rt, the reaction mixture was poured into brine and the product extracted with EtOAc (2×), dried over Na2SO4, concentrated in vacuo, and purified by flash chromatography over silica gel (EtOAc/Hex, 4/6) to afford tert-butyl 4-[4-(4-amino-1,2,5-oxadiazol-3-yl)phenyl]piperazine-1-carboxylate.

後処理

  1. temperaturethe reaction was refluxed overnight
  2. temperaturethe reaction was refluxed for 2 hours
  3. temperaturethe reaction was refluxed for 1 hour
  4. temperaturethe reaction was refluxed for 3 hours
  5. extractionthe product extracted with EtOAc (2×)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. custompurified by flash chromatography over silica gel (EtOAc/Hex, 4/6)

出典と根拠

ORDレコード
ord-e7db718def9e4c408bcf41be36ee34f1
出典データセット
uspto-grants-2006_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07012075B2

反応ノート

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