Ethanol → Phosphoric acid--methyl 5-amino-4-oxopentanoate (1/1)

HRID 222817Notes

Reaction equation

HRID 222817 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:11])[CH2:5][CH2:6][C:7]([CH2:9][NH2:10])=[O:8].[P:12](=[O:16])([OH:15])([OH:14])[OH:13].C(N(CC)CC)C.C(O)C>O>[P:12]([OH:16])([OH:15])([OH:14])=[O:13].[CH3:2][O:3][C:4](=[O:11])[CH2:5][CH2:6][C:7]([CH2:9][NH2:10])=[O:8]

Participants

6

Reactant 4

HCID 702EthanolHCID 1004Phosphoric AcidHCID 8471TriethylamineHCID 157921Methyl Aminolevulinate Hydrochloride

Product 1

HCID 71423951Phosphoric acid--methyl 5-amino-4-oxopentanoate (1/1)

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 30 g (165 mmol) portion of δ-aminolevulinic acid methyl ester hydrochloride and 20.9 g (181 mmol) of 85% phosphoric acid were dissolved in 30 ml of purified water, and 17.5 g (173 mmol) of triethylamine was added dropwise thereto while stirring on an ice bath. 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 17 hours under a reduced pressure. A 37 g (154 mmol) portion of δ-aminolevulinic acid methyl ester phosphate was obtained at a yield of 93 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 17 hours under a reduced pressure

Sources & evidence

ORD record
ord-3c0eb6482767484690aef54b979e8d69
Source dataset
uspto-grants-2012_06
Patent number
US08207376B2

Reaction notes

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