Ammonia → HCID 54408428, compound

HRID 1416876Notes

Reaction equation

HRID 1416876 reaction equation
[C:1]1([C@@H:7]2[CH2:12][CH2:11][O:10][C:8]2=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH3:13].ClCCl.CO>C(O)C>[C:1]1([C@H:7]([CH2:12][CH2:11][OH:10])[C:8]([NH2:13])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 13000824HCID 13000824, compoundHCID 21226129Dichloromethane methanol

Product 1

HCID 54408428HCID 54408428, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(S)-2-phenylbutyrolactone (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 (S)-2-phenyl-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-2cb38e23fb4f4c4981bb9a3ea3f809b7
Source dataset
uspto-grants-1999_06
Patent number
US05916786

Reaction notes

Loading…