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Sodium Hydroxide → 6-[(E)-N-hydroxy-C-[(2R)-2-(2-methylphenyl)-2-(4-methylsulfonylphenyl)ethyl]carbonimidoyl]-2-methylpyridazin-3-one

HRID 1527980
ノート
印刷プレビュー

反応式

HRID 1527980 の反応式
[NH:1]1CCC[C@H]1C(O)=O.[OH-:9].[Na+].Br[C:12]1[CH:17]=[CH:16][C:15]([C@H:18]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[CH3:39])[CH2:19][C:20]2([C:25]3[CH:26]=[CH:27][C:28](=[O:32])[N:29]([CH3:31])[N:30]=3)OCCO2)=[CH:14][CH:13]=1.[CH3:40][S:41]([O-:43])=[O:42].[Na+]>[Cu]I.CS(C)=O>[OH:9]/[N:1]=[C:20](/[C:25]1[CH:26]=[CH:27][C:28](=[O:32])[N:29]([CH3:31])[N:30]=1)\[CH2:19][C@H:18]([C:15]1[CH:16]=[CH:17][C:12]([S:41]([CH3:40])(=[O:43])=[O:42])=[CH:13][CH:14]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[CH3:39]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 14798Sodium HydroxideHCID 145742L-ProlineHCID 2733271Sodium methanesulfinateHCID 86684810(R)-6-(2-(2-(4-Bromophenyl)-2-o-tolylethyl)-1,3-dioxolan-2-yl)-2-methylpyridazin-3(2H)-one

生成物 1

HCID 1366450646-[(E)-N-hydroxy-C-[(2R)-2-(2-methylphenyl)-2-(4-methylsulfonylphenyl)ethyl]carbonimidoyl]-2-methylpyridazin-3-one収率 36.2%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 679Dimethyl Sulfoxide溶媒

実験手順

L-proline (7.5 mg, 65 μmol) was combined with dimethyl sulfoxide (1 ml), then sodium hydroxide (2.6 mg, 65 μmol) was added and the reaction stirred at room temperature for 30 min, then (R)-6-(2-(2-(4-bromophenyl)-2-o-tolylethyl)-1,3-dioxolan-2-yl)-2-methylpyridazin-3(2H)-one (37 mg, 81 μmol), sodium methanesulfinate (68 mg, 650 μmol) and copper(I) iodide (12.4 mg, 65 μmol) were added. The reaction mixture was heated at 120° C. for 22 h, then partitioned between water and ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and evaporated. Chromatography (SiO2; gradient heptane-ethyl acetate) produced the title compound (10 mg, 27%). White semisolid, MS: 455.2 [M+H]+.

後処理

  1. temperatureThe reaction mixture was heated at 120° C. for 22 h
  2. custompartitioned between water and ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

出典と根拠

ORDレコード
ord-8a1c10869cf34673b332e4db3a4704e1
出典データセット
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09090565B2

反応ノート

読み込み中…

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