Carbon Dioxide → 335203-10-6

Temperature

118 °C

To a 25-ml flask was added 4.0 g (0.044 mole) of the (S)-PM-2/(R)-PM-1 mixture with 0.02 g anhydrous zinc chloride. A reflux condenser with drying tube was attached and 4.7 g (0.046 mole) acetic anhydride was added by lifting the drying tube momentarily. The mixture was refluxed at about 118° C. for 2 hours and then allowed to cool. GC-analysis of a 1% solution in water showed a single peak for PMA-2 with retention time matching the first peak observed for commercial PMA-2 enantiomers. These results indicated that the first PMA-2 peak is the (S) enantiomer. A single peak was also observed for the PMA-1 enantiomer. This peak also matched the first peak for PMA-1, present in ˜3% in the commercial mixture, indicating that it was (R)-2-methoxy-1-propanol acetate. These results indicate that the (R) and (S) PMA-1 enantiomers exhibit opposite elution order from that observed for the corresponding PMA-2 enantiomers. The mixture was neutralized by adding 2.44 g (0.024 mole) anhydrous sodium carbonate and stirring for approximately 1 hour with CO2 evolution. A short path distillation head was attached and the reaction product was distilled using a heat gun as heat source. About 5.0 g material boiling in the 95-137° C. range was collected. GC analysis showed sample purity to be about 95% (S-PMA-2 92.6% and R-PMA-1 2.7%).

1. customA reflux condenser with drying tube
2. temperatureto cool
3. distillationA short path distillation head
4. distillationthe reaction product was distilled
5. temperatureas heat source
6. customboiling in the 95-137° C. range
7. customwas collected

ORD record

ord-417f44332050444786e1f55e0f722648

Source dataset

uspto-grants-2007_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07264960B2