Tetrahydrofuran → HCID 86630235, Verbindung

HRID 641989Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 641989
C(OC(=O)/C=C/[C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[CH:14][N:13]([C:19]1[CH:20]=[C:21]([CH:26]=[CH:27][C:28]=1[CH3:29])[C:22]([O:24][CH3:25])=[O:23])[C:12]2=[O:30])(C)(C)C.I([O-])(=O)(=O)=O.[Na+].C1C[O:41][CH2:40]C1>O.C(O)(C)(C)C.[Os](=O)(=O)(=O)=O>[CH:40]([C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[CH:14][N:13]([C:19]1[CH:20]=[C:21]([CH:26]=[CH:27][C:28]=1[CH3:29])[C:22]([O:24][CH3:25])=[O:23])[C:12]2=[O:30])=[O:41]

Komponenten

7

Edukt 3

HCID 8028Tetrahydrofuran2×HCID 23667635Sodium periodateHCID 68511776methyl 3-[6-[(1E)-3-tert-butoxy-3-oxoprop-1-en-1-yl]-4-oxoquinazolin-3(4H)-yl]-4-methylbenzoate

Produkt 1

HCID 86630235HCID 86630235, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 30318Osmium TetroxideKatalysatorHCID 962WaterLösungsmittelHCID 6386tert-ButanolLösungsmittel

Versuchsvorschrift

To a mixture of methyl 3-[6-[(1E)-3-tert-butoxy-3-oxoprop-1-en-1-yl]-4-oxoquinazolin-3(4H)-yl]-4-methylbenzoate (1.11 g) and sodium periodate (1.24 g) in THF (20 ml) and water (6 ml) was added 2.5% wt solution of osmium tetroxide in tert-butanol (0.34 ml). The reaction was stirred at room temperature for 72 hours, diluted with THF (30 ml) and the precipitate removed by filtration. The resultant solution was concentrated and the residue dissolved in ethyl acetate, washed water/brine mixture, 10% aqueous solution of sodium thiosulfate (×2) and brine. The organic layers were concentrated to give a solid which was triturated with iso-hexane and collected by filtration to give methyl 3-(6-formyl-4-oxoquinazolin-3(4H)-yl)-4-methylbenzoate as a solid (0.54 g). NMR Spectrum: (DMSOd6) 2.21 (s, 3H), 3.88 (s, 3H), 7.64 (d, 1H), 7.93 (d, 1H), 8.05 (m, 1H), 8.11 (d, 1H), 8.32 (m, 1H), 8.48 (s, 1H), 8.77 (d, 1H), 10.19 (s, 1H); Mass Spectrum: M+H+ 323.

Aufarbeitung

  1. customthe precipitate removed by filtration
  2. concentrationThe resultant solution was concentrated
  3. dissolutionthe residue dissolved in ethyl acetate
  4. washwashed water/brine mixture, 10% aqueous solution of sodium thiosulfate (×2) and brine
  5. concentrationThe organic layers were concentrated
  6. customto give a solid which
  7. customwas triturated with iso-hexane
  8. filtrationcollected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-50e7c9b4821d472d8673124b7a4c1ac8
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07696215B2

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