4-Aminobenzoic Acid → Pseudoephedrine
Reaction equation
C(O)[C@H]1O[C@H](O[C@]2(CO)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@@H]1O.P([O-])([O-])(O)=O.[K+].[K+].P([O-])(O)(O)=O.[K+].NC1C=CC(C(O)=O)=CC=1.P([O-])([O-])([O-])=O.[Na+].[Na+].[Na+].Cl.[CH3:56][NH:57][CH:58]([CH3:67])[C:59]([C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1)=[O:60].O=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O>>[CH3:67][C@H:58]([NH:57][CH3:56])[C@@H:59]([OH:60])[C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1Participants
Reactant 7
Product 1
Conditions
- Temperature
- 30 °C
Procedure
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.
Workup
- customto give bacterial cells, they
- customwere placed into a test tube
- additionTo this were added dl-
- customAfter the reaction
- customto remove bacterial cells
Sources & evidence
- ORD record
- ord-68f0c3cf698f444fb6cbd6e268a2fc7a
- Source dataset
- uspto-grants-2004_12
- Patent number
- US06835559B2
Reaction notes
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