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Trifluoroacetic acid → (6-Methoxy-4-oxo-7-(piperidin-4-ylmethoxy)quinazolin-3(4H)-yl)methyl pivalate

HRID 238099
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 238099
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][O:15][C:16]2[CH:25]=[C:24]3[C:19]([C:20](=[O:34])[N:21]([CH2:26][O:27][C:28](=[O:33])[C:29]([CH3:32])([CH3:31])[CH3:30])[CH:22]=[N:23]3)=[CH:18][C:17]=2[O:35][CH3:36])[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:36][O:35][C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][C:16]=1[O:15][CH2:14][CH:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1)[N:23]=[CH:22][N:21]([CH2:26][O:27][C:28](=[O:33])[C:29]([CH3:30])([CH3:31])[CH3:32])[C:20]2=[O:34]
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Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 11733854tert-Butyl 4-(((6-methoxy-4-oxo-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-7-yl)oxy)methyl)piperidine-1-carboxylate

Produkt 1

HCID 11058522(6-Methoxy-4-oxo-7-(piperidin-4-ylmethoxy)quinazolin-3(4H)-yl)methyl pivalateAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 7-(1-(tert-butoxycarbonyl)piperidin-4-ylmethoxy)-6-methoxy-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (2.32 g, 4.6 mmol) in methylene chloride (23 ml) containing TFA (5 ml) was stirred at ambient temperature for 1 hour. The volatiles were removed under vacuum. The residue was partitioned between ethyl acetate and sodium hydrogen carbonate. The organic solvent was removed under vacuum and the residue was filtered. The precipitate was washed with water, and dried under vacuum. The solid was azeotroped with toluene and dried under vacuum to give 6-methoxy-7-(piperidin-4-ylmethoxy)-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (1.7 g, 92%).

Aufarbeitung

  1. customThe volatiles were removed under vacuum
  2. customThe residue was partitioned between ethyl acetate and sodium hydrogen carbonate
  3. customThe organic solvent was removed under vacuum
  4. filtrationthe residue was filtered
  5. washThe precipitate was washed with water
  6. customdried under vacuum
  7. customThe solid was azeotroped with toluene
  8. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-24915922e87748be958856d9d2366fbd
Quelldatensatz
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08642608B2

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