Hydrochloric Acid → 5-((4-Bromo-2-formylphenyl)(4-methoxybenzyl)amino)pentanoic acid

HRID 402268노트

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HRID 402268 반응식
[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:6]([CH2:7][N:8]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]2=[O:14])=[CH:5][CH:4]=1.[OH-].[Na+].Cl.C(=O)([O-])[O-:21].[Na+].[Na+].[Br:26][C:27]1[CH:28]=[CH:29][C:30](F)=[C:31]([CH:34]=1)[CH:32]=[O:33]>CS(C)=O>[Br:26][C:27]1[CH:28]=[CH:29][C:30]([N:8]([CH2:7][C:6]2[CH:15]=[CH:16][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH2:13][CH2:12][CH2:11][CH2:10][C:9]([OH:21])=[O:14])=[C:31]([CH:32]=[O:33])[CH:34]=1

참가 물질

7

반응물 5

HCID 313Hydrochloric Acid2회HCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 7363275-Bromo-2-fluorobenzaldehydeHCID 115068011-(4-Methoxybenzyl)piperidin-2-one

생성물 1

HCID 114954475-((4-Bromo-2-formylphenyl)(4-methoxybenzyl)amino)pentanoic acid수율 96.6%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
0 °C

실험 절차

To 1-(4-methoxybenzyl)piperidin-2-one (50.0 g) was added aqueous 4N sodium hydroxide solution (228 ml) and then the mixture was refluxed for a day. The mixture was cooled to 0° C. and concentrated hydrochloric acid (76 ml) was added thereto. The mixture was neutralized. Then, after adding sodium carbonate (53.8 g) and dimethyl sulfoxide (600 ml), 5-bromo-2-fluorobenzaldehyde (38.6 g) was added dropwise at 135° C. to the mixture. After refluxing for 5 hours, the mixture was neutralized with 3N hydrochloric acid at 0° C., and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, after which it was dried with magnesium sulfate. The solvent was distilled off under reduced pressure to give 5-((4-bromo-2-formylphenyl)(4-methoxybenzyl)amino)pentanoic acid (77.2 g) as a brown oily material.

후처리

  1. temperaturethe mixture was refluxed for a day
  2. additionwas added dropwise at 135° C. to the mixture
  3. temperatureAfter refluxing for 5 hours
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water and saturated brine
  6. dry with materialafter which it was dried with magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure

출처 및 근거

ORD 기록
ord-3fe3d86cb0404120a56ed88219c1cb6a
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08741943B2

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