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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2308167Generated: October 29, 2026

4-Aminobenzoic Acid → Pseudoephedrine

https://huagongshe.com/reaction/2308167

Reaction equation

Participants

RoleNameHCIDCharge
Reactant4-Aminobenzoic AcidHCID 978—
ReactantSucroseHCID 5988—
ReactantTrisodium PhosphateHCID 24243—
ReactantPotassium Phosphate, DibasicHCID 24450—
Reactant(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 107526—
Reactant(+/-)-2-(Methylamino)propiophenone hydrochlorideHCID 458517—
ReactantMonobasic potassium phosphateHCID 516951—
ProductPseudoephedrineHCID 70287%

Reaction Conditions

Temperature30 °C

Reaction Steps

Rhodococcus erythropolis MAK-34 was inoculated to 5 ml of a medium (pH 7.0) containing 1.0% saccharose, 0.5% corn steep liquor, 0.1% dipotassium hydrogenphosphate, 0.3% potassium dihydrogenphosphate, 0.01% p-aminobenzoic acid and each inducer; and shake-culturing was carried out at 30° C. for 48 hours. After the culture was centrifuged to give bacterial cells, they were placed into a test tube and suspended by adding 1.0 ml of 0.2 M sodium phosphate buffer (pH 7.0) thereto. To this were added dl-2-methylamino-1-phenyl-1-propanone hydrochloride (10 mg) and glucose (20 mg) and reaction was allowed to take place under shaking at 30° C. for 16 hours. After the reaction, the reaction solution was centrifuged to remove bacterial cells, and the supernatant was subjected to HPLC, producing optically active pseudoephedrine (μ Bondaspherephenyl manufactured by Waters Inc.; diameter of 4 mm; length of 150 mm; eluent—7% acetonitrile-0.05 M sodium phosphate buffer (pH 6.5); flow rate of 0.8 ml/min; detection wavelength at 220 nm). As shown in Table 12, the production displayed remarkably higher values than does the case without the addition of inducer.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06835559B2
Source datasetuspto-grants-2004_12
ORD IDord-68f0c3cf698f444fb6cbd6e268a2fc7a
Source noteuspto-grants-2004_12