Sodium ethoxide → (+)-N-(7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-2-ethoxymethyl-isonicotinamide

HRID 985816ノート

反応式

HRID 985816 の反応式
Cl[CH2:2][C:3]1[CH:4]=[C:5]([CH:26]=[CH:27][N:28]=1)[C:6]([NH:8][C:9]1[S:10][C:11]2[C:17]([CH:18]3[CH2:23][O:22][CH2:21][CH2:20][O:19]3)=[CH:16][CH:15]=[C:14]([O:24][CH3:25])[C:12]=2[N:13]=1)=[O:7].[CH3:29][CH2:30][O-:31].[Na+]>C(O)C>[O:19]1[CH2:20][CH2:21][O:22][CH2:23][CH:18]1[C:17]1[C:11]2[S:10][C:9]([NH:8][C:6](=[O:7])[C:5]3[CH:26]=[CH:27][N:28]=[C:3]([CH2:2][O:31][CH2:30][CH3:29])[CH:4]=3)=[N:13][C:12]=2[C:14]([O:24][CH3:25])=[CH:15][CH:16]=1

参加物

4

反応物 2

HCID 2723922Sodium ethoxideHCID 22507718(+)-2-chloromethyl-N-(7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-isonicotinamide

生成物 1

HCID 22507700(+)-N-(7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-2-ethoxymethyl-isonicotinamide収率 68%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of 50 mg (0.12 mmol) (+)-2-chloromethyl-N-(7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-isonicotinamide in 2 ml ethanol was added 1.32 ml (3.57 mmol) sodium ethylate solution (2.71 M solution in ethanol) and the mixture ultrasonicated at room temperature for 2 h. The reaction mixture was then poured onto water and extracted three times with dichloromethane. The organic phases were dried over sodium sulfate and concentrated in vacuo. Flash chromatography (1/1 acetone/heptane) followed by trituration in ether afforded 35 mg (68%) (+)-N-(7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-2-ethoxymethyl-isonicotinamide as an off-white solid. [α]D20=+60.7° (c=0.94, CHCl3), ES-MS m/e (%): 430 (M+H+, 100).

後処理

  1. customthe mixture ultrasonicated at room temperature for 2 h
  2. additionThe reaction mixture was then poured onto water
  3. extractionextracted three times with dichloromethane
  4. dry with materialThe organic phases were dried over sodium sulfate
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-666d9d58983e43b6bccae8250fdea770
出典データセット
uspto-grants-2005_03
特許番号
US06872833B2

反応ノート

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