L-Alanine → HCID 86583776, compound

HRID 988985Notes

Reaction equation

HRID 988985 reaction equation
S(Cl)([Cl:3])=O.[CH:5]1([CH2:8][OH:9])[CH2:7][CH2:6]1.[NH2:10][C@H:11]([C:13](O)=[O:14])[CH3:12]>>[ClH:3].[CH:5]1([CH2:8][O:9][C:13](=[O:14])[C@H:11]([CH3:12])[NH2:10])[CH2:7][CH2:6]1

Participants

4

Reactant 3

HCID 5950L-AlanineHCID 24386Thionyl ChlorideHCID 75644Cyclopropanemethanol

Product 1

HCID 86583776HCID 86583776, compoundYield 85%

Procedure

Thionyl chloride (1.2 ml, 0.017 M) was added dropwise to a stirred solution of cyclopropyl methanol (6.8 ml, 8.4 mmol) 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: 0.75 g, 8.4 mmol) 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 orange/red oil which was repeatedly triturated and coevaporated with diethyl ether, to remove traces of cyclopropyl methanol. Diethyl ether (200 ml) was added and the mixture was stirred for 30 min. The resulting suspension was filtered to give the product as a cream solid (1.29 g, 7.1 mmol, 85%).

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 orange/red oil which
  5. customwas repeatedly triturated
  6. customto remove traces of cyclopropyl methanol
  7. additionDiethyl ether (200 ml) was added
  8. stirringthe mixture was stirred for 30 min
  9. filtrationThe resulting suspension was filtered

Sources & evidence

ORD record
ord-1c5190c1bf5349e5a075986ba666ea23
Source dataset
uspto-grants-2003_10
Patent number
US06638919B2

Reaction notes

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