Pyridine → HCID 22719618, 화합물

HRID 48443노트

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HRID 48443 반응식
[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]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 22719625HCID 22719625, 화합물

생성물 1

HCID 22719618HCID 22719618, 화합물수율 92.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

2-(tert-butoxycarbonylamino)-5-hydroxyindan (100 mg, 0.40 mmol) synthesized in Reference Production 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:

후처리

  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)

출처 및 근거

ORD 기록
ord-aae33df9b3724cfa954fe8fb305dfd55
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06703421B1

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