Water → HCID 57063652, compound

HRID 1457263Notes

Reaction equation

HRID 1457263 reaction equation
[H-].[Na+].[NH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C[O:11][C:12](=O)[C@@H:13]1[O:15][C@H:14]1[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1.O>CS(C)=O>[CH3:23][O:22][C:19]1[CH:18]=[CH:17][C:16]([C@@H:14]2[O:15][C@H:13]2[C:12]([NH:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[O:11])=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6115AnilineHCID 24758Sodium hydrideHCID 158607Methyl (2R,3S)-3-(4-methoxyphenyl)-2-oxiranecarboxylate

Product 1

HCID 57063652HCID 57063652, compoundYield 55.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent3×

Procedure

To a mixture of sodium hydride (62.5% oil dispersion, 0.46 g) and dimethyl sulfoxide (3 ml) is added a solution of aniline (1.02 g) in dimethyl sulfoxide (1 ml) at room temperature under nitrogen atmosphere, and the mixture is stirred for 30 minutes. To the mixture is added a solution of (2R,3S)-3-(4-methoxyphenyl)-2,3-epoxypropionic acid methyl ester (2.08 g) in dimethyl sulfoxide (4 ml) at room temperature over a period of 15 minutes. The mixture is further stirred at the same temperature for one hour, and thereto is added water (50 ml). The precipitated yellow crystals are collected by filtration, and recrystallized from ethyl acetate (60 ml) to give (2R,3S)-3-(4-methoxyphenyl)-2,3-epoxy-N-phenylpropionamide (1.50 g).

Workup

  1. stirringThe mixture is further stirred at the same temperature for one hour
  2. filtrationThe precipitated yellow crystals are collected by filtration
  3. customrecrystallized from ethyl acetate (60 ml)

Sources & evidence

ORD record
ord-4e1556240a2841fd8b9c13302d1ac54d
Source dataset
uspto-grants-1998_12
Patent number
US05847122

Reaction notes

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