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

HRID 25682

反応式

HRID 25682 の反応式
[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

参加物

6

反応物 3

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

生成物 1

HCID 69754033tert-butyl ((4R)-2-benzhydryl-4-phenyl-oxazolidin-3-yl)-acetate収率 114.1%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-baf8df1b87c8452ebbf4cdc0f2992acd
出典データセット
uspto-grants-2005_02
特許番号
US06858591B2

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