Water → HCID 67079001, compound

HRID 240802Notes

Reaction equation

HRID 240802 reaction equation
CCl.[NH2:3][CH2:4][C:5](=[O:11])[CH2:6][CH2:7][C:8]([OH:10])=[O:9].[CH2:12](N(CC)CC)C.[C:19](Cl)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O>ClCCl>[CH3:12][O:9][C:8](=[O:10])[CH2:7][CH2:6][C:5]([CH2:4][NH:3][C:19](=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:11]

Participants

6

Reactant 4

HCID 962WaterHCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 86664626HCID 86664626, compound

Product 1

HCID 67079001HCID 67079001, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under a nitrogen atmosphere, a solution of 5-aminolevulinic acid methyl hydrochloride (1.0 g, 5.5 mmol) and triethylamine (2.3 mL, 16.5 mmol) in dichloromethane (50 mL) was cooled to 0° C., and benzoyl chloride (0.7 mL, 6.1 mmol) was then added to the solution. The obtained mixture was stirred at room temperature for 3 hours. Thereafter, water was added to the reaction solution, and it was then extracted with ethyl acetate. The organic layer was washed with a saturated saline and was then dried over sodium sulfate. The solvent was distilled away, and the obtained residue was then purified by silica gel column chromatography (hexane/ethyl acetate), so as to obtain the title compound (1.29 g, yield: 94%).

Workup

  1. extractionwas then extracted with ethyl acetate
  2. washThe organic layer was washed with a saturated saline
  3. dry with materialwas then dried over sodium sulfate
  4. distillationThe solvent was distilled away
  5. customthe obtained residue was then purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-2e13ebb443cc41fcafd3d3a3a561f50d
Source dataset
uspto-grants-2014_02
Patent number
US08648103B2

Reaction notes

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