Aniline → HCID 11345649, compound

HRID 898827Notes

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].[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CS(O)(=O)=O>C(OCC)(=O)C>[C:13]1([NH:12][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:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 3-crotonoyl-1,3-oxazolidin-2-one (155 mg, 1.0 mmol) in ethyl acetate (3 ml) in a stream of nitrogen was added Pd((R)-binap)(H2O)2(OTf)2 (26.6 mg, 0.025 mmol), and the resulting mixture was cooled to 0° C. Aniline (0.11 ml, 1.2 mmol) was added to the mixture, and to the solution was added slowly methanesulfonic acid (0.078 ml, 1.2 mmol). Then, the cooling ice-bath was removed and the reaction mixture was reacted at room temperature for 18 hours with stirring. After completion of the reaction, the solvent was evaporated off, and the crude product obtained was purified by a silica gel column chromatography (hexane:ethyl acetate=1:1) to give the objective compound 3-(3-phenylaminobutyryl)-oxazolidin-2-one (37 mg, 15% yield). Enantiomeric excess ratio of this product was determined by a liquid chromatography using a column for separation of optical isomers (column: AD-H) to be 82% e.e.

Workup

customThen, the cooling ice-bath was removed
customthe reaction mixture was reacted at room temperature for 18 hours
customAfter completion of the reaction
customthe solvent was evaporated off
customthe crude product obtained
customwas purified by a silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record: ord-4e21057441bd464b81c919238e62c8f9
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07351849B2

Reaction notes

Loading…