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

HRID 32289노트

반응식

HRID 32289 반응식
[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]

참가 물질

4

반응물 1

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

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3514f385e6c745acbd2c1ed07ba20415
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07427390B2

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