Ammonia → (2S,3R)-3-(4-methylphenyl)-2,3-epoxypropionamide

HRID 1457257Notes

Reaction equation

HRID 1457257 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.[NH3:15]>CO>[CH3:13][C:10]1[CH:11]=[CH:12][C:7]([C@H:5]2[O:6][C@@H:4]2[C:3]([NH2:15])=[O:2])=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 10176494(2S,3R)-3-(4-methylphenyl)-2,3-epoxypropionic acid methyl ester

Product 1

HCID 10866888(2S,3R)-3-(4-methylphenyl)-2,3-epoxypropionamideYield 76.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a mixture of (2S,3R)-3-(4-methylphenyl)-2,3-epoxypropionic acid methyl ester (3.84 g) and methanol (25 ml) is added dropwise a solution of 28% aqueous ammonia (6.1 g) in methanol (10 ml) under ice-cooling. The reaction mixture is gradually warmed to room temperature, and stirred for two hours, and further stirred for one hour under ice-cooling. The precipitated crystals are collected by filtration, washed, and dried at 50° C. to give (2S,3R)-3-(4-methylphenyl)-2,3-epoxypropionamide (2.71 g).

Workup

  1. temperaturecooling
  2. stirringfurther stirred for one hour under ice-
  3. temperaturecooling
  4. filtrationThe precipitated crystals are collected by filtration
  5. washwashed
  6. customdried at 50° C.

Sources & evidence

ORD record
ord-4cf2fa88699b4a8985e21ac4af7cb1f2
Source dataset
uspto-grants-1998_12
Patent number
US05847122

Reaction notes

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