P-Anisidine → 3-[3-(4-methoxyphenylamino)butyryl]-1,3-oxazolidin-2-one

HRID 898829Notes

Reaction equation

HRID 898829 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].[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=1>C1(C)C=CC=CC=1>[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][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:16][CH:15]=1

Participants

4

Reactant 2

HCID 7732P-AnisidineHCID 5365845HCID 5365845, compound

Product 1

HCID 121794903-[3-(4-methoxyphenylamino)butyryl]-1,3-oxazolidin-2-oneYield 82%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of Pd((R)-binap)(OH2)2(OTf)2 (26.6 mg, 0.025 mmol) in toluene (3 ml) were added 3-crotonoyl-1,3-oxazolidin-2-one (155 mg, 1.0 mmol) and anisidine (148 mg, 1.2 mmol). After the resulting mixture was stirred at room temperature for 3 hours, the reaction solution was concentrated and purified by a silica gel column chromatography (hexane:ethyl acetate=4:1) to give the objective 3-[3-(4-methoxyphenylamino)butyryl]-1,3-oxazolidin-2-one (228 mg, 82% yield).

Workup

  1. concentrationthe reaction solution was concentrated
  2. custompurified by a silica gel column chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-16c9d29046b24e7583a665bc9bc0e557
Source dataset
uspto-grants-2008_04
Patent number
US07351849B2

Reaction notes

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