Lithium hydroxide, monohydrate → 3-[(3-Methyl-4-oxo-3,4-dihydro-2H-1,3-benzoxazin-7-yl)oxy]-5-[(3S)-tetrahydrofuran-3-yloxy]benzoic acid

HRID 548734Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 548734
O.[OH-].[Li+].[CH3:4][N:5]1[C:10](=[O:11])[C:9]2[CH:12]=[CH:13][C:14]([O:16][C:17]3[CH:18]=[C:19]([CH:24]=[C:25]([O:27][C@H:28]4[CH2:32][CH2:31][O:30][CH2:29]4)[CH:26]=3)[C:20]([O:22]C)=[O:21])=[CH:15][C:8]=2[O:7][CH2:6]1>O.C1COCC1>[CH3:4][N:5]1[C:10](=[O:11])[C:9]2[CH:12]=[CH:13][C:14]([O:16][C:17]3[CH:18]=[C:19]([CH:24]=[C:25]([O:27][C@H:28]4[CH2:32][CH2:31][O:30][CH2:29]4)[CH:26]=3)[C:20]([OH:22])=[O:21])=[CH:15][C:8]=2[O:7][CH2:6]1

Komponenten

5

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 57663180methyl 3-[(3-methyl-4-oxo-3,4-dihydro-2H-1,3-benzoxazin-7-yl)oxy]-5-[(3S)-tetrahydrofuran-3-yloxy]benzoate

Produkt 1

HCID 576631863-[(3-Methyl-4-oxo-3,4-dihydro-2H-1,3-benzoxazin-7-yl)oxy]-5-[(3S)-tetrahydrofuran-3-yloxy]benzoic acidAusbeute 95,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Lithium hydroxide monohydrate (13 mg, 0.3 mmol) in water (2.5 mL) was added to a solution of methyl 3-[(3-methyl-4-oxo-3,4-dihydro-2H-1,3-benzoxazin-7-yl)oxy]-5-[(3S)-tetrahydrofuran-3-yloxy]benzoate (0.12 g, 0.3 mmol) in THF (5 mL) and stirred at RT for 20 hours. The THF was removed in vacuo and the aqueous layer was washed with ethyl acetate (50 mL) to remove any impurities. The aqueous layer was acidified and extracted into ethyl acetate (2×50 mL), washed with brine (50 mL), dried (MgSO4), and the solvent removed in vacuo to give the desired compound as a white solid (110 mg).

Aufarbeitung

  1. customThe THF was removed in vacuo
  2. washthe aqueous layer was washed with ethyl acetate (50 mL)
  3. customto remove any impurities
  4. extractionextracted into ethyl acetate (2×50 mL)
  5. washwashed with brine (50 mL)
  6. dry with materialdried (MgSO4)
  7. customthe solvent removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-48bb7e981e74423fab58e65937850657
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07943607B2

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