Ammonia → (R)-3-(2-(2-(tert-Butyldimethylsilyloxy)-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethylamino)-2-methylpropyl)benzaldehyde

HRID 1689519Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1689519
C(=O)([O:7][C:8]1[CH:9]=[CH:10][C:11]([C@@H:19]([O:34][Si:35]([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36])[CH2:20][NH:21][C:22]([CH3:33])([CH3:32])[CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([CH:30]=[O:31])[CH:25]=2)=[C:12]2[C:17]=1[NH:16][C:15](=[O:18])[CH:14]=[CH:13]2)OC(C)(C)C.N>CO>[Si:35]([O:34][C@H:19]([C:11]1[CH:10]=[CH:9][C:8]([OH:7])=[C:17]2[C:12]=1[CH:13]=[CH:14][C:15](=[O:18])[NH:16]2)[CH2:20][NH:21][C:22]([CH3:33])([CH3:32])[CH2:23][C:24]1[CH:25]=[C:26]([CH:27]=[CH:28][CH:29]=1)[CH:30]=[O:31])([C:38]([CH3:39])([CH3:40])[CH3:41])([CH3:37])[CH3:36]

Komponenten

4

Edukt 2

HCID 222AmmoniaHCID 57989095(r)-Tert-butyl 5-(1-(tert-butyldimethylsilyloxy)-2-(1-(3-formylphenyl)-2-methylpropan-2-ylamino)ethyl)-2-oxo-1,2-dihydroquinolin-8-yl carbonate

Produkt 1

HCID 57989117(R)-3-(2-(2-(tert-Butyldimethylsilyloxy)-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethylamino)-2-methylpropyl)benzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of (R)-tert-butyl 5-(1-(tert-butyldimethylsilyloxy)-2-(1-(3-formylphenyl)-2-methylpropan-2-ylamino)ethyl)-2-oxo-1,2-dihydroquinolin-8-yl carbonate (Example 275, step g) (0.42 g) in methanol (15 mL) was treated with ammonia (35% aqueous) (2 mL). The reaction mixture was allowed to stand for 3 hours at 20° C. The solvent was removed under a stream of nitrogen and the residue was partitioned between ethyl acetate and brine. The aqueous layer was extracted with ethyl acetate and the combined organics dried over sodium sulphate, filtered and the solvent evaporated under reduced pressure to afford the subtitled compound. Yield 0.34 g.

Aufarbeitung

  1. customThe solvent was removed under a stream of nitrogen
  2. customthe residue was partitioned between ethyl acetate and brine
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. dry with materialthe combined organics dried over sodium sulphate
  5. filtrationfiltered
  6. customthe solvent evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-cf2204806024436c8ec325836871587e
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08148373B2

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