Hydroxylamine → HCID 21708613, 화합물

HRID 1376495노트

반응식

HRID 1376495 반응식
[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

참가 물질

7

반응물 4

HCID 787HydroxylamineHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 21708661HCID 21708661, 화합물

생성물 1

HCID 21708613HCID 21708613, 화합물

시약·촉매·용매 2

HCID 887Methanol용매2회HCID 962Water용매

반응 조건

온도
40 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a72d37ab49024f9683927ee459e9c367
출처 데이터셋
uspto-grants-1997_09
특허 번호
US05663182

반응 노트

불러오는 중…