Water → Carbamic acid, N-[(1S)-1-[[(9-bromo-5-oxo-5H-[1]benzopyrano[3,4-c]pyridin-8-yl)oxy]methyl]-3-methylbutyl]-, 1,1-dimethylethyl ester

HRID 2369538Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2369538
[C:1]([O:5][C:6](=[O:30])[NH:7][C@@H:8]([CH2:26][CH:27]([CH3:29])[CH3:28])[CH2:9][O:10][C:11]1[CH:12]=[CH:13][C:14]2[C:24]3[C:19](=[CH:20][N:21]=[CH:22][CH:23]=3)[C:18](=[O:25])[O:17][C:15]=2[CH:16]=1)([CH3:4])([CH3:3])[CH3:2].C1C(=O)N([Br:38])C(=O)C1.O>C(#N)C>[C:1]([O:5][C:6](=[O:30])[NH:7][C@@H:8]([CH2:26][CH:27]([CH3:28])[CH3:29])[CH2:9][O:10][C:11]1[C:12]([Br:38])=[CH:13][C:14]2[C:24]3[C:19](=[CH:20][N:21]=[CH:22][CH:23]=3)[C:18](=[O:25])[O:17][C:15]=2[CH:16]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 86724438HCID 86724438, Verbindung

Produkt 1

HCID 86724437Carbamic acid, N-[(1S)-1-[[(9-bromo-5-oxo-5H-[1]benzopyrano[3,4-c]pyridin-8-yl)oxy]methyl]-3-methylbutyl]-, 1,1-dimethylethyl esterAusbeute 67,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a stirred solution of (S)-tert-butyl(4-methyl-1-((5-oxo-5H-chromeno[3,4-c]pyridin-8-yl)oxy)pentan-2-yl)carbamate (0.100 g, 0.242 mmol) (prepared as described in Example 11, Part E) in anhydrous acetonitrile (2 mL) was added NBS (0.043 g, 0.242 mmol) and the mixture heated to 80° C. for 12 h. After completion of reaction, water (10 mL) was added and extracted with ethyl acetate (2×20 mL). The combined organic extracts were dried over sodium sulfate and concentrated under reduced pressure to afford crude compound which was purified by preparative TLC to afford (S)-tert-butyl(1-((9-bromo-5-oxo-5H-chromeno[3,4-c]pyridin-8-yl)oxy)-4-methylpentan-2-yl)carbamate (80 mg, 0.163 mmol, 67% yield) as a pale yellow solid. LCMS (ESI) m/e 491.2 [(M+H)+, calcd for C23H28BrN2O5491.1] LC/MS retention time (method F): tR=1.12 min.

Aufarbeitung

  1. additionwas added
  2. extractionextracted with ethyl acetate (2×20 mL)
  3. dry with materialThe combined organic extracts were dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto afford crude compound which
  6. customwas purified by preparative TLC

Quellen und Nachweise

ORD-Eintrag
ord-c6db6ccf1dcc47ef9d0f67a5e3d35742
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08703953B2

Notizen zur Reaktion

Wird geladen…