Methylamine → (2S,3R)-3-(4-methylphenyl)-2,3-epoxy-N-methylpropionamide

HRID 1457259Notes

Reaction equation

HRID 1457259 reaction equation
C[O:2][C:3](=O)[C@H:4]1[O:6][C@@H:5]1[C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=1.[CH3:15][NH2:16]>CO>[CH3:13][C:10]1[CH:11]=[CH:12][C:7]([C@H:5]2[O:6][C@@H:4]2[C:3]([NH:16][CH3:15])=[O:2])=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 10176494(2S,3R)-3-(4-methylphenyl)-2,3-epoxypropionic acid methyl ester

Product 1

HCID 56977863(2S,3R)-3-(4-methylphenyl)-2,3-epoxy-N-methylpropionamideYield 91.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a mixture of (2S,3R)-3-(4-methylphenyl)-2,3-epoxypropionic acid methyl ester (1.92 g) and methanol (10 ml) is added dropwise a solution of 40% aqueous methylamine solution (2.37 g) in methanol (10 ml) under ice-cooling. The reaction mixture is stirred under ice-cooling for one hour, and concentrated under reduced pressure. To the residue is added ether, and the precipitated crystals are collected by filtration, washed, and dried at 50° C. to give (2S,3R)-3-(4-methylphenyl)-2,3-epoxy-N-methylpropionamide (1.75 g).

Workup

  1. temperaturecooling
  2. temperaturecooling for one hour
  3. concentrationconcentrated under reduced pressure
  4. additionTo the residue is added ether
  5. filtrationthe precipitated crystals are collected by filtration
  6. washwashed
  7. customdried at 50° C.

Sources & evidence

ORD record
ord-9db6e93a58d04a99a57f88bbadf95848
Source dataset
uspto-grants-1998_12
Patent number
US05847122

Reaction notes

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