Boron tribromide → 4-Acetylamino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-hydroxyphenyl)benzamide

HRID 2516

反応式

HRID 2516 の反応式
[C:1]([NH:4][C:5]1[CH:38]=[CH:37][C:8]([C:9]([N:11]([CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][CH:25]([C:28](=[O:36])[C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)[CH2:24][CH2:23]2)[C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18]C)[CH:13]=2)=[O:10])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].B(Br)(Br)Br.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:1]([NH:4][C:5]1[CH:38]=[CH:37][C:8]([C:9]([N:11]([CH2:20][CH2:21][N:22]2[CH2:23][CH2:24][CH:25]([C:28](=[O:36])[C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)[CH2:26][CH2:27]2)[C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[CH:13]=2)=[O:10])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

参加物

5

反応物 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 196899044-Acetylamino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-methoxyphenyl)benzamide

生成物 1

HCID 196897984-Acetylamino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-hydroxyphenyl)benzamide収率 76.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

4-Acetylamino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-methoxyphenyl)benzamide (50.0 mg, 0.10 mmol) was dissolved in methylene chloride (3.0 ml) to which was subsequently added a methylene chloride solution (1 ml) of boron tribromide (0.018 ml, 0.19 mmol) at 0° C. After 12 hours of stirring at 0° C. to room temperature, the reaction solution was mixed with saturated sodium bicarbonate aqueous solution and extracted with ethyl acetate. The resulting organic layer was washed with saturated sodium bicarbonate aqueous solution and saturated brine, and dried on anhydrous sodium sulfate. Thereafter, the solvent was distilled off under a reduced pressure, and the resulting residue was purified by a silica gel column chromatography (ethyl acetate-chloroform:methanol=10:1) to obtain 37.3 mg (76.7%) of the title compound in a light yellow amorphous form.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe resulting organic layer was washed with saturated sodium bicarbonate aqueous solution and saturated brine
  3. dry with materialdried on anhydrous sodium sulfate
  4. distillationThereafter, the solvent was distilled off under a reduced pressure
  5. customthe resulting residue was purified by a silica gel column chromatography (ethyl acetate-chloroform:methanol=10:1)

出典と根拠

ORDレコード
ord-afe5cbc25fd340cf8536ac9ee64ce538
出典データセット
uspto-grants-1998_03
特許番号
US05728835

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