Hydrochloric Acid → 1,5-anhydro-3-(6-bromo-1-methyl-4-oxo-1,4-dihydrobenzo[h]quinazolin-3(2H)-yl)-2,3-dideoxy-L-threo-pentitol

HRID 1183147Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1183147
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=13)[NH:8][CH2:7][N:6]([C@H:16]1[CH2:21][CH2:20][O:19][CH2:18][C@@H:17]1[O:22][Si](C(C)(C)C)(C)C)[C:5]2=[O:30].Cl.[C:32]([O-])(O)=O.[Na+]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=13)[N:8]([CH3:32])[CH2:7][N:6]([C@@H:16]1[C@@H:17]([OH:22])[CH2:18][O:19][CH2:20][CH2:21]1)[C:5]2=[O:30]

Komponenten

5

Edukt 3

HCID 313Hydrochloric Acid2×HCID 516892Sodium BicarbonateHCID 866903641,5-anhydro-3-(6-bromo-4-oxo-1,4-dihydrobenzo[h]quinazolin-3(2H)-yl)-2-O-[tert-butyl(dimethyl)silyl]-3,4-dideoxy-L-threo-pentitol

Produkt 1

HCID 866903661,5-anhydro-3-(6-bromo-1-methyl-4-oxo-1,4-dihydrobenzo[h]quinazolin-3(2H)-yl)-2,3-dideoxy-L-threo-pentitol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 1,5-anhydro-3-(6-bromo-4-oxo-1,4-dihydrobenzo[h]quinazolin-3(2H)-yl)-2-O-[tert-butyl(dimethyl)silyl]-3,4-dideoxy-L-threo-pentitol (0.89 g, 1.8 mmol) in THF (17.5 mL) was added hydrochloric acid (1 N, 10 mL). Additional concentrated hydrochloric acid (2 mL) was added. After stirring overnight, the solution was basified by addition of saturated, aqueous NaHCO3, then extracted 2× with EtOAc. The organics were washed with brine, dried over MgSO4, filtered, concentrated, and dried to provide 1,5-anhydro-3-(6-bromo-1-methyl-4-oxo-1,4-dihydrobenzo[h]quinazolin-3(2H)-yl)-2,3-dideoxy-L-threo-pentitol that gave a mass ion (ES+) of 392.9 for [M+H]+.

Aufarbeitung

  1. extractionextracted 2× with EtOAc
  2. washThe organics were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-7f0ac6c2cdda457ebce2e4d49e79c9ed
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08664234B2

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