Diethyl Ether → HCID 11460510, compound

HRID 1620763Notes

Reaction equation

HRID 1620763 reaction equation
[CH3:1][C:2]1([CH3:21])[N:6]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[C@@H:5]([C:17]([O:19]C)=O)[CH2:4][O:3]1.[Cl-].[NH4+].[CH2:24](OCC)[CH3:25]>CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4]>[OH:19][C:17]1([C@H:5]2[CH2:4][O:3][C:2]([CH3:1])([CH3:21])[N:6]2[C:7]([O:9][CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:8])[CH2:25][CH2:24]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 11066282HCID 11066282, compound

Product 1

HCID 11460510HCID 11460510, compound

Reagents, catalysts & solvents 1

HCID 11026Titanium isopropoxideCatalyst

Procedure

To a solution of 3-benzyl 4-methyl(4R)-2,2-dimethyl-1,3-oxazolidine-3,4-dicarboxylate (6.66 g) and titanium tetraisopropoxide (3.33 mL) in diethyl ether (200 mL) was added dropwise 3M ethyl magnesium bromide diethyl ether solution (18.9 mL) over 20 min under ice-cooling. The reaction mixture was stirred at room temperature overnight, and to the reaction mixture was added saturated aqueous ammonium chloride solution. The precipitated solid was removed by filtration. The filtrate was extracted with ethyl acetate, and the organic layer was separated, washed with saturated brine, dried over magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (2.52 g).

Workup

  1. temperaturecooling
  2. customThe precipitated solid was removed by filtration
  3. extractionThe filtrate was extracted with ethyl acetate
  4. customthe organic layer was separated
  5. washwashed with saturated brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-57fa84863c454e3199648cef42cbcced
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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