Ammonium Chloride → 3-[3-(4-methoxyphenylamino)butyryl]-1,3-oxazolidin-2-one

HRID 898832Notes

Reaction equation

HRID 898832 reaction equation
[C:1]([N:6]1[CH2:10][CH2:9][O:8][C:7]1=[O:11])(=[O:5])/[CH:2]=[CH:3]/[CH3:4].FC(F)(F)S(O)(=O)=O.[CH3:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([NH2:28])=[CH:24][CH:23]=1.[Cl-].[NH4+]>O1CCCC1>[CH3:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][CH:3]([CH3:4])[CH2:2][C:1]([N:6]2[CH2:10][CH2:9][O:8][C:7]2=[O:11])=[O:5])=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 5365845HCID 5365845, compoundHCID 86607687HCID 86607687, compound

Product 1

HCID 121794903-[3-(4-methoxyphenylamino)butyryl]-1,3-oxazolidin-2-oneYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a stream of nitrogen, a solution of 3-crotonoyl-1,3-oxazolidin-2-one (78 mg, 0.5 mmol), anisidine trifluoromethanesulfonate (205 mg, 0.75 mmol) and Pd((R)-binap)(μ-OH)]2(OTf)2 (4.6 mg, 0.0025 mmol) in tetrahydrofuran (0.5 mL) was stirred at room temperatures for 12 hours. When no starting material remained was observed, a saturated aqueous solution of ammonium chloride was added to quench the reaction, and the resulting mixture was extracted with ethyl acetate. The organic layer was concentrated and purified by a silica gel column chromatography (hexane:ethyl acetate=1:1) to give the objective 3-[3-(4-methoxyphenylamino)butyryl]-1,3-oxazolidin-2-one (128 mg, 92% yield). The enantiomeric excess ratio was determined to be 98% e.e. by a liquid chromatography with an optical isomer separating column (column: AD-H).

Workup

  1. customto quench
  2. customthe reaction
  3. extractionthe resulting mixture was extracted with ethyl acetate
  4. concentrationThe organic layer was concentrated
  5. custompurified by a silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-6e22917df6c34f35aabca0d75d3fc222
Source dataset
uspto-grants-2008_04
Patent number
US07351849B2

Reaction notes

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