N-(2-diethylamino-ethyl)-4-(2-benzyloxy-acetylamino)-2-methoxy-benzamide → N-(2-diethylamino-ethyl)-4-(2-hydroxy-acetylamino)-2-methoxy-benzamide

HRID 2262352ノート

反応式

HRID 2262352 の反応式
[CH2:1]([N:3]([CH2:29][CH3:30])[CH2:4][CH2:5][NH:6][C:7](=[O:28])[C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:25])[CH2:16][O:17]CC2C=CC=CC=2)=[CH:10][C:9]=1[O:26][CH3:27])[CH3:2]>CO.[Pd]>[CH2:29]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][NH:6][C:7](=[O:28])[C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:25])[CH2:16][OH:17])=[CH:10][C:9]=1[O:26][CH3:27])[CH3:30]

参加物

4

反応物 1

HCID 59793337N-(2-diethylamino-ethyl)-4-(2-benzyloxy-acetylamino)-2-methoxy-benzamide

生成物 1

HCID 59793338N-(2-diethylamino-ethyl)-4-(2-hydroxy-acetylamino)-2-methoxy-benzamide収率 22.6%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

340 mg (0.82 mmol) of N-(2-diethylamino-ethyl)-4-(2-benzyloxy-acetylamino)-2-methoxy-benzamide is mixed in 40 ml of methanol with 200 mg of palladium on carbon (10%), and it is hydrogenated for 1.5 hours at normal pressure and at room temperature. After the catalyst is drawn off on diatomaceous earth, the filtrate is concentrated by evaporation, and the residue is chromatographed on 10 g of Isolute NH2 (50 μm) with a gradient from methylene chloride. The correspondingly combined fractions are concentrated by evaporation and again on 20 g of Isolute NH2 (50 μm) with a gradient from cyclohexane to cyclohexane:methylene chloride=50:50, and 60 mg (22.6% of theory) of N-(2-diethylamino-ethyl)-4-(2-hydroxy-acetylamino)-2-methoxy-benzamide is obtained as an oil.

後処理

  1. concentrationthe filtrate is concentrated by evaporation
  2. customthe residue is chromatographed on 10 g of Isolute NH2 (50 μm) with a gradient from methylene chloride
  3. concentrationThe correspondingly combined fractions are concentrated by evaporation and again on 20 g of Isolute NH2 (50 μm) with a gradient from cyclohexane to cyclohexane

出典と根拠

ORDレコード
ord-3618f59660db464fa84f49d33eb400ae
出典データセット
uspto-grants-2010_12
特許番号
US07850948B2

反応ノート

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