Hydrochloric Acid → (S)-2-hydroxydecanoic acid

Participants

Reaction Steps

An alternate novel method of resolving 2-hydroxydecanoic acid is illustrated in scheme 3. According to this method, racemic 2-hydroxydecanoic acid (VI) is first converted to the racemic methyl ester (X) by reacting it with methanol and hydrochloric acid as described for the analogous reaction in scheme 2 (VIII→IX). The racemic methyl ester (X) is then reacted with Lipase P-30 to form (R)-methyl-2-hydroxydecanoate (IX) and (S)-2-hydroxydecanoic acid (VIII'). This reaction is typically carried out at a temperature from about 5° C. to about 55° C. in water or a water miscible solvent, or at the organic/aqueous interface of a water miscible solvent and an organic cosolvent. Examples of appropriate solvents are dimethylsulfoxide (DMSO)/water, toluene/water, methanol/water, hexane/water and tetrahydrofuran (THF)/water. The preferred temperature is from about 20° C. to about 50° C. and the preferred solvent is water. The pH is generally maintained at about 6.0 to about 8.0.

Provenance & Evidence