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

HRID 222818Notes

Reaction equation

HRID 222818 reaction equation
Cl.[CH2:2]([O:9][C:10](=[O:17])[CH2:11][CH2:12][C:13]([CH2:15][NH2:16])=[O:14])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[P:18](=[O:22])([OH:21])([OH:20])[OH:19].C(N(CC)CC)C.C(O)C>O>[P:18]([OH:22])([OH:21])([OH:20])=[O:19].[CH2:2]([O:9][C:10](=[O:17])[CH2:11][CH2:12][C:13]([CH2:15][NH2:16])=[O:14])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 1004Phosphoric AcidHCID 8471TriethylamineHCID 22253144Benzyl 5-amino-4-oxopentanoate--hydrogen chloride (1/1)

Product 1

HCID 66932752Phosphoric acid--benzyl 5-amino-4-oxopentanoate (1/1)

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 8 g (31 mmol) portion of δ-aminolevulinic acid benzyl ester hydrochloride and 4 g (34.7 mmol) of 85% phosphoric acid were dissolved in 8 ml of purified water, and 3.3 g (32.7 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, 300 ml of ethanol was added thereto and stirred. The thus precipitated precipitate was recovered by suction filtration and dried at room temperature for 16 hours under a reduced pressure. An 8.5 g (27 mmol) portion of δ-aminolevulinic acid benzyl ester phosphate was obtained at a yield of 87 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 16 hours under a reduced pressure

Sources & evidence

ORD record
ord-a356a005f0574bdca6fd9cd64faec519
Source dataset
uspto-grants-2012_06
Patent number
US08207376B2

Reaction notes

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