tert-Butyl {3-[4-cyano-2-dimethylcarbamoyl-5-methyl-6-phenyl-1,3-benzoxazol-7-yl]cyclopent-2-enyl}methylcarbamate → HCID 68585497, Verbindung

HRID 17627

Reaktionsgleichung

Reaktionsgleichung von HRID 17627
[C:1]([C:3]1[C:8]2[N:9]=[C:10]([C:12](=[O:16])[N:13]([CH3:15])[CH3:14])[O:11][C:7]=2[C:6]([C:17]2[CH2:21]C[CH:19]([CH2:22][NH:23][C:24](=O)OC(C)(C)C)[CH:18]=2)=[C:5]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:4]=1[CH3:37])#[N:2]>Cl.O1CCOCC1>[C:1]([C:3]1[C:8]2[N:9]=[C:10]([C:12]([N:13]([CH3:15])[CH3:14])=[O:16])[O:11][C:7]=2[C:6]([CH:17]2[CH2:18][CH2:19][C:22]([NH:23][CH3:24])=[CH:21]2)=[C:5]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:4]=1[CH3:37])#[N:2]

Komponenten

3

Edukt 1

HCID 86630887tert-Butyl {3-[4-cyano-2-dimethylcarbamoyl-5-methyl-6-phenyl-1,3-benzoxazol-7-yl]cyclopent-2-enyl}methylcarbamate

Produkt 1

HCID 68585497HCID 68585497, VerbindungAusbeute 59,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 204431481,4-Dioxane hydrochlorideLösungsmittel

Versuchsvorschrift

tert-Butyl {3-[4-cyano-2-dimethylcarbamoyl-5-methyl-6-phenyl-1,3-benzoxazol-7-yl]cyclopent-2-enyl}methylcarbamate (I-340-2) (154 mg, 0.31 mmol) was dissolved in 4 N hydrochloric acid/1,4-dioxane solution (3 ml), and stirred at room temperature for 1 hour. The solvent was evaporated away under reduced pressure, then ethanol was added to the resulting residue, followed by concentration under reduced pressure. This operation was repeated once again. The residue was dissolved in chloroform (15 ml) and an aqueous saturated sodium hydrogencarbonate solution (15 ml), and vigorously stirred for 10 minutes. The aqueous layer was separated, extracted twice with chloroform. The organic layers were combined, washed with saturated brine, and dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, the solvent was evaporated away, and the resulting residue was purified by preparative TLC (eluent, chloroform:methanol=9:1, v/v), and this was further purified by preparative TLC (eluent, chloroform:7 N ammonia-containing methanol solution=93:7, v/v) to obtain a brown solid (74 mg). The solid was washed in slurry with diisopropyl ether, and a pale brown solid was collected by filtration. The solid was dried at 60° C. under reduced pressure for 48 hours to obtain the entitled compound (57 mg, 46%).

Aufarbeitung

  1. customThe solvent was evaporated away under reduced pressure
  2. additionethanol was added to the resulting residue
  3. concentrationfollowed by concentration under reduced pressure
  4. dissolutionThe residue was dissolved in chloroform (15 ml)
  5. stirringan aqueous saturated sodium hydrogencarbonate solution (15 ml), and vigorously stirred for 10 minutes
  6. customThe aqueous layer was separated
  7. extractionextracted twice with chloroform
  8. washwashed with saturated brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. customThe insoluble matter was separated by filtration
  11. customthe solvent was evaporated away
  12. customthe resulting residue was purified by preparative TLC (eluent, chloroform
  13. custommethanol=9:1, v/v), and this was further purified by preparative TLC (eluent, chloroform
  14. addition7 N ammonia-containing methanol solution=93:7

Quellen und Nachweise

ORD-Eintrag
ord-c8f0c8b53ddf4901a85e341bb0c17443
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737166B2

Verknüpfte Notizen

Wird geladen…