Ethanol → (R)-8-Methyl-5-(4-nitrophenyl)-7-(5-methyl-1,3,4-oxadiazol-2-yl)-8,9-dihydro-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepine

HRID 25079

反応式

HRID 25079 の反応式
[CH3:1][C@@H:2]1[CH2:8][C:7]2[CH:9]=[C:10]3[O:15][CH2:14][O:13][C:11]3=[CH:12][C:6]=2[C:5]([C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=2)=[N:4][N:3]1[C:25]([NH:27][NH:28][C:29](=[O:31])[CH3:30])=S.C(O)C>ClCCl.C([O-])(=O)C.[Hg+2].C([O-])(=O)C>[CH3:1][C@@H:2]1[CH2:8][C:7]2[CH:9]=[C:10]3[O:15][CH2:14][O:13][C:11]3=[CH:12][C:6]=2[C:5]([C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=2)=[N:4][N:3]1[C:25]1[O:31][C:29]([CH3:30])=[N:28][N:27]=1

参加物

5

反応物 2

HCID 702EthanolHCID 86593813(R)-N'-(8-methyl-5-(4-nitrophenyl)-8,9-dihydro-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepin-7-carbothioyl)-acetic hydrazide

生成物 1

HCID 69436975(R)-8-Methyl-5-(4-nitrophenyl)-7-(5-methyl-1,3,4-oxadiazol-2-yl)-8,9-dihydro-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepine収率 51%

試薬・触媒・溶媒 2

HCID 15337Mercuric acetate触媒HCID 6344Dichloromethane溶媒

実験手順

A stirred mixture of 2.2 g (5.15 mmol) of (R)—N′-(8-methyl-5-(4-nitrophenyl)-8,9-dihydro-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepin-7-carbothioyl)-acetic hydrazide (an intermediate of method B of Example 28), 44 ml of ethanol and 1.72 g (5.39 mmol) of mercury (II) acetate was refluxed for 2 h. The residue obtained on concentration was dissolved in dichloromethane and filtered through a neutral aluminum oxide column. After washing the column the filtrate was concentrated and the residue was purified by column chromatography using silica gel (MN Kieselgel 60) as adsorbent and a mixture of n-hexane-ethyl acetate (1:2.5) as eluent to yield 1.07 g (51%) of the title compound. Mp.: 202-204° C. after recrystallization from ethanol. [α]: −249° (c=0.22; CHCl3).

後処理

  1. temperaturewas refluxed for 2 h
  2. customThe residue obtained on concentration
  3. filtrationfiltered through a neutral aluminum oxide column
  4. washAfter washing the column the filtrate
  5. concentrationwas concentrated
  6. customthe residue was purified by column chromatography
  7. additiona mixture of n-hexane-ethyl acetate (1:2.5) as eluent

出典と根拠

ORDレコード
ord-04778f73766b45f7825b9dbc3f96f606
出典データセット
uspto-grants-2005_02
特許番号
US06858605B2

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