Thionyl Chloride → cis-2-Pentenyl 5-aminolevulinate hydrochloride

HRID 218112

Reaction equation

HRID 218112 reaction equation
S(Cl)([Cl:3])=O.Cl.[NH2:6][CH2:7][C:8](=[O:14])[CH2:9][CH2:10][C:11]([OH:13])=[O:12]>CN(C)C=O>[ClH:3].[NH2:6][CH2:7][C:8](=[O:14])[CH2:9][CH2:10][C:11]([O:13][CH2:7]/[CH:8]=[CH:9]\[CH2:10][CH3:11])=[O:12]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 123608Aminolevulinic Acid Hydrochloride

Product 1

HCID 86632356cis-2-Pentenyl 5-aminolevulinate hydrochlorideYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

To 1 ml of thionyl chloride (SOCl2) were added 3 drops of N,N-dimethylformamide (DMF) with stirring. Following the addition of 5-aminolevulinic acid hydrochloride (ALA.HCl, 200 mg, 1.19 mol), the solution was stirred for 12 hours at room temperature. Concentration in a vacuum was conducted before the addition of cis-2-pentenol. Then, the reaction mixture was stirred for 1.5 hours at room temperature, followed by purification by silica gel chromatography to afford cis-2-pentenyl 5-aminolevulinate hydrochloride at a yield of 68%.

Workup

  1. stirringthe solution was stirred for 12 hours at room temperature
  2. concentrationConcentration in a vacuum
  3. additionwas conducted before the addition of cis-2-pentenol
  4. stirringThen, the reaction mixture was stirred for 1.5 hours at room temperature
  5. customfollowed by purification by silica gel chromatography

Sources & evidence

ORD record
ord-92f2949129df4026b4bef3e1ee5a7506
Source dataset
uspto-grants-2012_06
Patent number
US08198325B2

Linked notes

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