Diphenylacetaldehyde → tert-butyl ((4R)-2-benzhydryl-4-phenyl-oxazolidin-3-yl)-acetate

HRID 25682

Reaktionsgleichung

Reaktionsgleichung von HRID 25682
[OH:1][CH2:2][C@@H:3]([NH:10][CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:19]1([CH:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:26]=O)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.S([O-])([O-])(=O)=O.[Mg+2]>C(Cl)Cl.CCOCC>[CH:25]([CH:26]1[N:10]([CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C@H:3]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:2][O:1]1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Komponenten

6

Edukt 3

HCID 13696DiphenylacetaldehydeHCID 24083Sulfuric acid magnesium salt (1:1)HCID 59065869tert-butyl (S)-(2-hydroxy-1-phenyl-ethylamino)-acetate

Produkt 1

HCID 69754033tert-butyl ((4R)-2-benzhydryl-4-phenyl-oxazolidin-3-yl)-acetateAusbeute 114,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl (S)-(2-hydroxy-1-phenyl-ethylamino)-acetate (2.5 g, 10 mmole, obtained from Reference Example 9) in anhydrous methylene chloride (35 ml) were added diphenylacetaldehyde (2.16 g, 11 mmole) and magnesium sulfate (1.2 g, 10 mmole) under nitrogen. The resulting mixture was stirred at room temperature under nitrogen for 15 h, and diluted with ether. The organic layer was washed with saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated to dryness in vacuo. The oily residue was solidified upon standing, and recrystallized from ether/hexanes to give tert-butyl ((4R)-2-benzhydryl-4-phenyl-oxazolidin-3-yl)-acetate as a white solid (4.9 g, 98%).

Aufarbeitung

  1. washThe organic layer was washed with saturated sodium chloride solution
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated to dryness in vacuo
  5. customrecrystallized from ether/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-baf8df1b87c8452ebbf4cdc0f2992acd
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06858591B2

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