Methyl iodide → (2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-4-(dimethylcarbamoyl)-2-(methoxymethyl)-5,6-dihydropyridine-1 (2H)-carboxylate

HRID 627167ノート

反応式

HRID 627167 の反応式
[CH2:1]([O:4][N:5]([C@H:18]1[CH2:23][N:22]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C@H:21]([CH2:31][OH:32])[CH:20]=[C:19]1[C:33](=[O:37])[N:34]([CH3:36])[CH3:35])[S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-:17])=[O:16])(=[O:8])=[O:7])[CH:2]=[CH2:3].I[CH3:39]>C(#N)C.[Ag]=O>[CH2:1]([O:4][N:5]([C@H:18]1[CH2:23][N:22]([C:24]([O:26][C:27]([CH3:29])([CH3:30])[CH3:28])=[O:25])[C@H:21]([CH2:31][O:32][CH3:39])[CH:20]=[C:19]1[C:33](=[O:37])[N:34]([CH3:35])[CH3:36])[S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-:17])=[O:16])(=[O:8])=[O:7])[CH:2]=[CH2:3]

参加物

5

反応物 2

HCID 6328Methyl iodideHCID 89852042(2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-4-(dimethylcarbamoyl)-2-(hydroxymethyl)-5,6-dihydropyridine-1(2H)-carboxylate2 回

生成物 1

HCID 89851960(2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-4-(dimethylcarbamoyl)-2-(methoxymethyl)-5,6-dihydropyridine-1 (2H)-carboxylate収率 98%

試薬・触媒・溶媒 2

HCID 92152Silver(II) oxide触媒HCID 6342Acetonitrile溶媒

実験手順

(2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-4-(dimethylcarbamoyl)-2-(hydroxymethyl)-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 139, 1.64 g, 3.03 mmol) and silver oxide (2.81 g, 12.13 mmol) were dissolved in acetonitrile (40 mL). To this solution was added iodomethane (1.897 mL, 30.34 mmol) under N2 and stirred over for 5 days protected from the light. The reaction mixture was then filtered through Celite, rinsed with EtOAc, and the crude product was loaded onto silica gel. The product was purified by flash chromatography (0-20% MeOH/DCM) to yield the desired product (1.643 g, 98%) as an off-white solid.

後処理

  1. filtrationThe reaction mixture was then filtered through Celite
  2. washrinsed with EtOAc
  3. customThe product was purified by flash chromatography (0-20% MeOH/DCM)

出典と根拠

ORDレコード
ord-9299cfd2bd314880bb84e91ce18f6a80
出典データセット
uspto-grants-2016_04
特許番号
US09309245B2

反応ノート

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