Tetrahydrofuran → HCID 178452623, Verbindung

HRID 1064202Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1064202
[C:1]([O:5][C:6](=[O:24])[NH:7][C:8]1[CH:9]=[C:10]2[C:22](=[O:23])[NH:21][N:20]=[CH:19][C:12]3=[C:13]([CH:17]=C)[NH:14][C:15]([CH:16]=1)=[C:11]23)([CH3:4])([CH3:3])[CH3:2].[O:25]1CCCC1.C([O-])([O-])=O.[K+].[K+].I([O-])(=O)(=O)=O.[Na+]>C(OCC)(=O)C.O>[C:1]([O:5][C:6](=[O:24])[NH:7][C:8]1[CH:9]=[C:10]2[C:22](=[O:23])[NH:21][N:20]=[CH:19][C:12]3=[C:13]([CH:17]=[O:25])[NH:14][C:15]([CH:16]=1)=[C:11]23)([CH3:2])([CH3:3])[CH3:4]

Komponenten

7

Edukt 4

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 23667635Sodium periodateHCID 136141708(6-Oxo-2-vinyl-5,6-dihydro-1h-[1,2]diazepino[4,5,6-cd]indol-8-yl)-carbamic acid tert-butyl ester

Produkt 1

HCID 178452623HCID 178452623, VerbindungAusbeute 22 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel4×HCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

To a solution of the title compound of Example 164 (48 mg, 0.146 mmol) in 1:1 tetrahydrofuran:H2O (4 mL) was added K2CO3 (30 mg, 0.219 mmol), K2OSO2(OH)4 (7 mg) and K3Fe(CN)6 (72 mg, 0.219 mmol). The mixture was stirred at room temperature for 2 hours whereupon water and ethyl acetate were added. Following extractive work-up, the organic layer was then dried, filtered, and concentrated. The residue was dissolved in 1:1 tetrahydrofuran:H2O (2 mL) and sodium periodate (156 mg, 50.73 mmol) was added. The mixture was stirred at room temperature for 30 min whereupon water and ethyl acetate were added. Following extractive work-up, the organic layer was then dried, filtered, and concentrated. Silica gel chromatography of the residue, eluting with 30% ethyl acetate in hexane gave Intermediate 230(a) as a pale yellow solid (11 mg, 0.034 mmol) in 22% yield.

Aufarbeitung

  1. additionwere added
  2. customthe organic layer was then dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in 1:1 tetrahydrofuran
  6. additionwere added
  7. customthe organic layer was then dried
  8. filtrationfiltered
  9. concentrationconcentrated
  10. washSilica gel chromatography of the residue, eluting with 30% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-860dcb08235e4f73a959542eeb555b76
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06967198B2

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