Ammonia → (2S,3S)-2 ethyl-3-hydroxybutyramide

HRID 1586299Notes

Reaction equation

HRID 1586299 reaction equation
[CH2:1]([C@@H:3]([C@@H:9]([OH:11])[CH3:10])[C:4](OCC)=[O:5])[CH3:2].[NH3:12]>C(O)C>[CH2:1]([C@@H:3]([C@@H:9]([OH:11])[CH3:10])[C:4]([NH2:12])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 13215287(2S,3S)-Ethyl 2 ethyl-3-hydroxybutyrate

Product 1

HCID 11829477(2S,3S)-2 ethyl-3-hydroxybutyramideYield 85.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(2S,3S)-Ethyl 2 ethyl-3-hydroxybutyrate (1 gram) is dissolved in 5 ml of absolute ethanol followed by the addition of 0.5 gram of gaseous ammonia. The solution is kept in a stoppered flask, and the progress of the reaction is followed by thin layer chromatography. After the reaction is judged complete, the ethanol is evaporated and the resulting residue redissolved in ethyl acetate. Ammonia is removed by extraction with 1% HCl, and the ethyl acetate solution is dried over MgSO4, filtered, and rotary evaporated to leave 0.7 grams of (2S,3S)-2 ethyl-3-hydroxybutyramide.

Workup

  1. customThe solution is kept in a stoppered flask
  2. customthe ethanol is evaporated
  3. dissolutionthe resulting residue redissolved in ethyl acetate
  4. customAmmonia is removed by extraction with 1% HCl
  5. dry with materialthe ethyl acetate solution is dried over MgSO4
  6. filtrationfiltered
  7. customrotary evaporated

Sources & evidence

ORD record
ord-8ad26da8a07a40f5a378a9c9369f7788
Source dataset
uspto-grants-1999_08
Patent number
US05942644

Reaction notes

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