Ammonia → Pentanoic acid, 5-amino-4-oxo-, 4-methylbenzenesulfonate

HRID 1922333Notes

Reaction equation

HRID 1922333 reaction equation
Cl.Cl.[NH2:3][CH2:4][C:5](=[O:11])[CH2:6][CH2:7][C:8]([OH:10])=[O:9].N.O.[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20]([OH:23])(=[O:22])=[O:21])=[CH:16][CH:15]=1>O>[C:14]1([CH3:24])[CH:15]=[CH:16][C:17]([S:20]([OH:23])(=[O:21])=[O:22])=[CH:18][CH:19]=1.[NH2:3][CH2:4][C:5](=[O:11])[CH2:6][CH2:7][C:8]([OH:10])=[O:9]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 123608Aminolevulinic Acid HydrochlorideHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 11623627Pentanoic acid, 5-amino-4-oxo-, 4-methylbenzenesulfonate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A column was charged with 180 ml of a strongly acidic ion exchange resin (AMBERLITE IR120B Na, manufactured by Japan Organo). The ion exchange resin was used after converting it from sodium ion type to hydrogen ion type through a hydrochloric acid treatment. Next, 36.00 g (215 mmol) of 5-aminolevulinic acid hydrochloride was dissolved in 1800 ml of ion exchange water and passed through said column, and then 1000 ml of ion exchange water was passed through the same. Next, 1 N aqueous ammonia was slowly passed through the same to collect 555 ml of yellow eluate. The thus collected eluate was mixed with 81.72 g (430 mmol) of p-toluenesulfonic acid monohydrate and concentrated using an evaporator. To the concentrated liquid, 400 ml of acetone was added, followed by vigorously stirring with a stirrer and then the mixture was allowed to stand still at 4° C. for 16 hours. The thus precipitated solid was recovered by suction filtration and washed with 400 ml of acetone. The thus obtained solid was dried under reduced pressure for 12 hours to obtain 47.78 g (158 mmol) of the substance of interest. Its physical property data are shown below.

Workup

  1. additionA column was charged with 180 ml of a strongly acidic ion exchange resin (AMBERLITE IR120B Na, manufactured by Japan Organo)
  2. customto collect 555 ml of yellow eluate
  3. concentrationconcentrated
  4. customan evaporator
  5. additionTo the concentrated liquid, 400 ml of acetone was added
  6. filtrationThe thus precipitated solid was recovered by suction filtration
  7. washwashed with 400 ml of acetone
  8. customThe thus obtained solid was dried under reduced pressure for 12 hours
  9. customto obtain 47.78 g (158 mmol) of the substance of interest

Sources & evidence

ORD record
ord-313bd94a40aa4bffbc3e5568ca6e0d1a
Source dataset
uspto-grants-2012_05
Patent number
US08173839B2

Reaction notes

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