5-Aminolevulinic Acid → Propyl 5-amino-4-oxopentanoate--hydrogen chloride (1/1)

HRID 491232Notes

Reaction equation

HRID 491232 reaction equation
[ClH:1].[NH2:2][CH2:3][C:4](=[O:10])[CH2:5][CH2:6][C:7]([OH:9])=[O:8].N[CH2:12][C:13](=O)[CH2:14]CC(O)=O>C(O)CC.Cl>[ClH:1].[NH2:2][CH2:3][C:4](=[O:10])[CH2:5][CH2:6][C:7]([O:9][CH2:12][CH2:13][CH3:14])=[O:8]

Participants

5

Reactant 2

HCID 1375-Aminolevulinic AcidHCID 123608Aminolevulinic Acid Hydrochloride

Product 1

HCID 18386169Propyl 5-amino-4-oxopentanoate--hydrogen chloride (1/1)

Reagents, catalysts & solvents 2

HCID 10311-PropanolCatalystHCID 313Hydrochloric AcidSolvent

Conditions

Temperature
75 °C

Procedure

0.5 g 5-aminolevulinic acid hydrochloride was dissolved in 100 ml dry n-propanol containing 1-2 drops of conc. hydrochloride in a 250 ml glass reactor equipped with a stirrer, reflux condenser and a thermometer. The reaction mixture was stirred at 70-80° C. for approx. 20 hours. After all the 5-aminolevulinic acid was converted to its n-propylester (followed by 1H-NMR), the excess propanol was removed, and the product dried under high vacuum (<1 mBar) at 40-50° C. The reaction gave 0.49 g propyl 5-aminolevulinate hydrochloride. The structure was confirmed by 1H-NMR in DMSO-d6.

Workup

  1. customequipped with a stirrer
  2. temperaturereflux condenser
  3. customthe excess propanol was removed
  4. customthe product dried under high vacuum (<1 mBar) at 40-50° C

Sources & evidence

ORD record
ord-f43dac3588704a488561ee99962987c0
Source dataset
uspto-grants-2009_05
Patent number
US07530461B2

Reaction notes

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