Pyridine → HCID 22719618, Verbindung

HRID 48443Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 48443
[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]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 22719625HCID 22719625, Verbindung

Produkt 1

HCID 22719618HCID 22719618, VerbindungAusbeute 92,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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:

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-aae33df9b3724cfa954fe8fb305dfd55
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06703421B1

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