Water → Methyl 5-((4-bromo-2-formylphenyl)(4-methoxybenzyl)amino)pentanoate

HRID 1928938ノート

反応式

HRID 1928938 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)[CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[C:4]([CH:25]=[O:26])[CH:3]=1.[C:27](=O)([O-])[O-].[K+].[K+].IC.O>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:16][C:17]2[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=2)[CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:27])=[O:14])=[C:4]([CH:25]=[O:26])[CH:3]=1

参加物

6

反応物 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 114954475-((4-Bromo-2-formylphenyl)(4-methoxybenzyl)amino)pentanoic acid

生成物 1

HCID 11575669Methyl 5-((4-bromo-2-formylphenyl)(4-methoxybenzyl)amino)pentanoate収率 57.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

To a solution of 5-((4-bromo-2-formylphenyl)(4-methoxybenzyl)amino)pentanoic acid (77.2 g) and potassium carbonate (30.5 g) in DMF (500 ml) was added dropwise a solution of iodomethane (36.5 g) in DMF (100 ml) at 0° C. under nitrogen atmosphere. After stirring for 2 hours, water was added and the mixture was extracted with ethyl acetate. After washing the organic layer with water three times and with saturated brine once, the resultant was dried with magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1→hexane:ethyl acetate=4:1) to give methyl 5-((4-bromo-2-formylphenyl)(4-methoxybenzyl)amino)-pentanoate (45.7 g) as a brown oily material.

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washAfter washing the organic layer with water three times
  3. dry with materialwith saturated brine once, the resultant was dried with magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1→hexane:ethyl acetate=4:1)

出典と根拠

ORDレコード
ord-d28b8ec295cd482aa0ef6e0b206c8aeb
出典データセット
uspto-grants-2012_05
特許番号
US08183273B2

反応ノート

読み込み中…