Chloride → HCID 90044568, compound

HRID 988984Notes

Reaction equation

HRID 988984 reaction equation
[Cl-:1].[CH3:2][CH2:3][CH:4]([OH:7])[CH2:5][CH3:6].[NH2:8][C@H:9]([C:11](O)=[O:12])[CH3:10]>>[ClH:1].[CH3:2][CH2:3][CH:4]([O:7][C:11](=[O:12])[C@H:9]([CH3:10])[NH2:8])[CH2:5][CH3:6]

Participants

4

Procedure

Tionyl chloride (1.6 ml, 0.022 M) was added dropwise to a stirred solution of 3-pentanol (18.2 ml, 0.17 M) at 0° C. under nitrogen. The mixture was stirred for 30 minutes, then allowed to warm to room temperature. L-Alanine (pre-dried at 60° C. over P2O5 for 4 hrs: 1.0 g, 0.011 M) was added and the resulting suspension was heated at reflux overnight (the reaction mixture became a clear, colourless solution). The solvent was removed under reduced pressure to leave an oil which was repeatedly triturated and coevaporated with diethyl ether, then petrol (60/80) to remove traces of 3-pentanol. The resulting oily residue solidified on drying under high vacuum to give a peach-coloured solid (1.96 g, 10 mmol, 89%).

Workup

  1. temperaturethe resulting suspension was heated
  2. temperatureat reflux overnight (the reaction mixture
  3. customThe solvent was removed under reduced pressure
  4. customto leave an oil which
  5. customwas repeatedly triturated
  6. custompetrol (60/80) to remove traces of 3-pentanol
  7. customon drying under high vacuum

Sources & evidence

ORD record
ord-e74a4653d52b4ea0b5229a93da107fb9
Source dataset
uspto-grants-2003_10
Patent number
US06638919B2

Reaction notes

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