Hydroxylamine → HCID 21708613、化合物

HRID 1376495ノート

反応式

HRID 1376495 の反応式
[C:1](O)(=O)[C:2]([OH:4])=[O:3].Cl[C:8]1([C:16]2[C:17](Cl)=[N:18]S[N:20]=2)[CH:13]2[CH2:14][CH2:15][N:10]([CH2:11][CH2:12]2)[CH2:9]1.[NH2:22][OH:23].[O:24]=P(Cl)(Cl)Cl.[OH-:29].[Na+]>CO.O>[C:2]([OH:4])(=[O:3])/[CH:1]=[CH:16]/[C:17]([OH:24])=[O:29].[NH2:18][C:17]1[C:16]([CH:8]2[CH:13]3[CH2:12][CH2:11][N:10]([CH2:15][CH2:14]3)[CH2:9]2)=[N:20][O:23][N:22]=1

参加物

7

反応物 4

HCID 787HydroxylamineHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 21708661HCID 21708661、化合物

生成物 1

HCID 21708613HCID 21708613、化合物

試薬・触媒・溶媒 2

HCID 887Methanol溶媒2 回HCID 962Water溶媒

反応条件

温度
40 °C

実験手順

To a solution of crude (1-azabicyclo[2.2.21octan-3-yl)hydroxyiminoacetonitrile (10 g, max. 29 mmol) (example 1 C) in methanol (50 ml) was added a methanol solution of hydroxylamine (prepared from NH2OH, HCl (4.2 g, 60 mmol) in methanol (60 ml) and sodium (1.38 g, 60 mmol) in methanol (60 ml)). The reaction mixture was stirred at 40° C. for 18 h and evaporated to give the crude amide oxime derivative. The residue was treated with excess of POCl3 at 45° C. for 18 h. Water and sodium hydroxide was added to obtain alkaline pH and the aqueous mixture extracted with chloroform. The combined organic phases were dried and evaporated to give the free base of the title compound as a solid (yield 570 mg). MS: M+ : 194. Crystallization as the fumarate salt from isopropanol gave the title compound (110 mg) (Compound 66), M.p. 60°-75° C.

後処理

  1. customevaporated
  2. customto give the crude amide oxime derivative
  3. customto obtain alkaline pH
  4. extractionthe aqueous mixture extracted with chloroform
  5. customThe combined organic phases were dried
  6. customevaporated

出典と根拠

ORDレコード
ord-a72d37ab49024f9683927ee459e9c367
出典データセット
uspto-grants-1997_09
特許番号
US05663182

反応ノート

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