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Sodium Bicarbonate → HCID 135977444、化合物

HRID 1964612
ノート
印刷プレビュー

反応式

HRID 1964612 の反応式
[N:1]1([C:5]([C:7]2[CH:36]=[CH:35][C:10]([O:11][C:12]3[CH:13]=[C:14]([C:24]4[NH:28][C:27]([C:29]5[O:30][C:31]([CH3:34])=[N:32][N:33]=5)=[CH:26][CH:25]=4)[CH:15]=[C:16]([O:18][C@@H:19]([CH3:23])[CH2:20][O:21]C)[CH:17]=3)=[C:9]([F:37])[CH:8]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1.B(Br)(Br)Br.ClCCl.C(=O)([O-])O.[Na+]>ClCCl>[N:1]1([C:5]([C:7]2[CH:36]=[CH:35][C:10]([O:11][C:12]3[CH:17]=[C:16]([CH:15]=[C:14]([C:24]4[NH:28][C:27]([C:29]5[O:30][C:31]([CH3:34])=[N:32][N:33]=5)=[CH:26][CH:25]=4)[CH:13]=3)[O:18][C@@H:19]([CH3:23])[CH2:20][OH:21])=[C:9]([F:37])[CH:8]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 516892Sodium BicarbonateHCID 22277759Boron tribromide dichloromethaneHCID 135977445HCID 135977445、化合物

生成物 1

HCID 135977444HCID 135977444、化合物収率 21%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

2-(5-{3-[4-(Azetidin-1-ylcarbonyl)-2-fluorophenoxy]-5-[(1S)-2-methoxy-1-methylethoxy]phenyl}-1H-pyrrol-2-yl)-5-methyl-1,3,4-oxadiazole (379.2 mg, 0.748 mmol) synthesized in Example (66i) was dissolved in dichloromethane (15 mL), and a boron tribromide/dichloromethane solution (1M, 750 μL, 0.75 mmol) was added at −78° C. under nitrogen atmosphere, followed by stirring at 0° C. for 3 hours. To the reaction solution, a saturated aqueous sodium hydrogencarbonate solution was added, and extraction was carried out with ethyl acetate. The organic layer was washed with saturated brine, and subsequently dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: methanol/dichloromethane=2%-8%) to afford the desired compound (76.9 mg, yield 21%) as a pale yellow solid.

後処理

  1. extractionextraction
  2. washThe organic layer was washed with saturated brine
  3. dry with materialsubsequently dried over sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe resulting residue was purified
  6. washsilica gel column chromatography (elution solvent: methanol/dichloromethane=2%-8%)

出典と根拠

ORDレコード
ord-ba4084d6ef3c4dfb997bdbcf7f55611e
出典データセット
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08415359B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート