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

HRID 1810777ノート

反応式

HRID 1810777 の反応式
[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

参加物

7

反応物 5

HCID 313Hydrochloric Acid2 回HCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 7363275-Bromo-2-fluorobenzaldehydeHCID 115068011-(4-Methoxybenzyl)piperidin-2-one

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-7284bd1cd98a4512a708493859e8b653
出典データセット
uspto-grants-2013_01
特許番号
US08362058B2

反応ノート

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