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

HRID 25682

반응식

HRID 25682 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-baf8df1b87c8452ebbf4cdc0f2992acd
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06858591B2

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