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

HRID 355646Notes

Reaction equation

HRID 355646 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) was dissolved in 5 ml of absolute ethanol, followed by the addition of 0.5 gram of gaseous ammonia. The solution was kept in a stoppered flask, and the progress of the reaction was followed by thin layer chromatography. After the reaction was judged complete, the ethanol was evaporated and the resulting residue redissolved in ethyl acetate. Ammonia was removed by extraction with 1% HCl, and the ethyl acetate solution was dried over MgSO4, filtered, and rotary evaporated to leave 0.7 grams of (2S,3S)-2 ethyl-3-hydroxybutyramide.

Workup

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

Sources & evidence

ORD record
ord-ff73b715d23c4b3ebd839108e5efb3e2
Source dataset
uspto-grants-1998_11
Patent number
US05834261

Reaction notes

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