Ethanol → Aminolevulinic acid phosphate

HRID 222819

Reaction equation

HRID 222819 reaction equation
Cl.[NH2:2][CH2:3][C:4](=[O:10])[CH2:5][CH2:6][C:7]([OH:9])=[O:8].[P:11](=[O:15])([OH:14])([OH:13])[OH:12].N1C=CC(C)=CC=1.C(O)C>O>[P:11]([OH:15])([OH:14])([OH:13])=[O:12].[NH2:2][CH2:3][C:4](=[O:10])[CH2:5][CH2:6][C:7]([OH:9])=[O:8]

Participants

6

Reactant 4

HCID 702EthanolHCID 1004Phosphoric AcidHCID 79634-MethylpyridineHCID 123608Aminolevulinic Acid Hydrochloride

Product 1

HCID 24737828Aminolevulinic acid phosphate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 10.05 g (60.6 mmol) portion of δ-aminolevulinic acid hydrochloride and 4.5 ml (65.7 mmol) of 85% phosphoric acid were dissolved in 30 ml of purified water, and 5.83 g (62.7 mmol) of γ-picoline was added dropwise thereto while stirring. After completion of the dropwise addition and subsequent stirring at room temperature for 10 minutes, 400 ml of ethanol was added thereto and stirred. The thus precipitated precipitate was recovered by suction filtration and dried at room temperature for 19 hours under a reduced pressure. A 10.55 g (46.1 mmol) portion of δ-aminolevulinic acid phosphate was obtained at a yield of 77 mol %.

Workup

  1. additionAfter completion of the dropwise addition
  2. stirringsubsequent stirring at room temperature for 10 minutes
  3. stirringstirred
  4. filtrationThe thus precipitated precipitate was recovered by suction filtration
  5. customdried at room temperature for 19 hours under a reduced pressure

Sources & evidence

ORD record
ord-901946f65deb420a9baf0c01fe95683c
Source dataset
uspto-grants-2012_06
Patent number
US08207376B2

Linked notes

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