Ammonia → HCID 55284513, compound

HRID 1416873Notes

Reaction equation

HRID 1416873 reaction equation
[CH3:1][C@H:2]1[C@@H:7]([CH3:8])[CH2:6][O:5][C:3]1=[O:4].[NH3:9].ClCCl.CO>C(O)C>[CH3:1][C@@H:2]([C@@H:7]([CH3:8])[CH2:6][OH:5])[C:3]([NH2:9])=[O:4]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 10877084HCID 10877084, compoundHCID 21226129Dichloromethane methanol

Product 1

HCID 55284513HCID 55284513, compoundYield 60.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(2S,3R)-2,3-dimethylbutyrolactone (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 (eluent dichloromethane/methanol 20:1). 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,3R)-2,3-dimethyl-4-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-b580dba7d2da4b83af0cf72efede018e
Source dataset
uspto-grants-1999_06
Patent number
US05916786

Reaction notes

Loading…