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

HRID 1928938노트

반응식

HRID 1928938 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-d28b8ec295cd482aa0ef6e0b206c8aeb
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08183273B2

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