Pyridine → HCID 22719618、化合物

HRID 1582009ノート

反応式

HRID 1582009 の反応式
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([OH:18])[CH:15]=2)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.[C:25](Cl)(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(Cl)Cl>[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:18][C:25](=[O:32])[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:15]=2)[CH2:10]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 3

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 22719625HCID 22719625、化合物

生成物 1

HCID 22719618HCID 22719618、化合物収率 92.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

2-(tert-butoxycarbonylamino)-5-hydroxyindan (100 mg, 0.40 mmol) synthesized in Preparation Example 1 was dissolved in dry methylene chloride (2 ml), to which pyridine (0.15 ml, 1.8 mmol) and benzoyl chloride (0.14 ml, 1.1 mmol) were added, and the mixture was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure, to which diethylether was added. The organic layer was washed with, in the order of, an aqueous solution of saturated potassium hydrogen sulfate, brine, an aqueous solution of saturated sodium hydrogen carbonate, and brine, and then was dried over anhydrous sodium sulfate. The residue obtained by distilling off the solvent under reduced pressure was purified by silica gel chromatography (hexane:ethyl acetate=3:1) to obtain 2-(tert-butoxycarbonylamino)-5-benzoyloxyindan (130 mg, 0.37 mmol) having the following physical properties:

後処理

  1. additionwere added
  2. concentrationThe reaction mixture was concentrated under reduced pressure, to which diethylether
  3. additionwas added
  4. washThe organic layer was washed with, in the order of, an aqueous solution of saturated potassium hydrogen sulfate, brine
  5. dry with materialan aqueous solution of saturated sodium hydrogen carbonate, and brine, and then was dried over anhydrous sodium sulfate
  6. customThe residue obtained
  7. distillationby distilling off the solvent under reduced pressure
  8. customwas purified by silica gel chromatography (hexane:ethyl acetate=3:1)

出典と根拠

ORDレコード
ord-16b24a069f63460e8eada146364fa01e
出典データセット
uspto-grants-2004_05
特許番号
US06734180B1

反応ノート

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