Water → 3-Phenyl-propynoic acid phenyl-(3,4,5-trimethoxy-benzyl)-amide

HRID 1623471노트

반응식

HRID 1623471 반응식
[C:1]1([NH:7][C:8](=[O:17])[C:9]#[C:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:19][C:20]1[CH:21]=[C:22]([O:30][CH3:31])[C:23]([O:28][CH3:29])=[C:24]([O:26][CH3:27])[CH:25]=1.C([O-])([O-])=O.[Cs+].[Cs+].O>CN(C=O)C>[C:1]1([N:7]([CH2:19][C:20]2[CH:21]=[C:22]([O:30][CH3:31])[C:23]([O:28][CH3:29])=[C:24]([O:26][CH3:27])[CH:25]=2)[C:8](=[O:17])[C:9]#[C:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 10796Cesium carbonateHCID 305965N,3-diphenylprop-2-ynamideHCID 103552715-(Bromomethyl)-1,2,3-trimethoxybenzene

생성물 1

HCID 670362353-Phenyl-propynoic acid phenyl-(3,4,5-trimethoxy-benzyl)-amide수율 65%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

3-Phenyl-propynoic acid phenylamide (951.4 mg, 4.3 mmol), 5-bromomethyl-1,2,3-trimethoxy-benzene (1.35 g, 5.16 mmol), and Cs2CO3 (2.1 g, 6.45 mmol) were dissolved in DMF (20 ml). The mixture was stirred at room temperature for 16 h. The mixture was poured into water and extracted with ethyl acetate, dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification was by flash column chromatography on silica gel, eluting with hexanes-EtOAc (6:1 and then 4:1) afforded 3-phenyl-propynoic acid phenyl-(3,4,5-trimethoxy-benzyl)-amide 1.03 g (65%).

후처리

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customPurification
  5. washeluting with hexanes-EtOAc (6:1

출처 및 근거

ORD 기록
ord-5ca7e5b5e7fb40daac691d1c0f043b88
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08778973B2

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