Hydrochloric Acid → (S)-2-hydroxydecanoic acid
Reaktionsgleichung
[OH:1][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[C:3]([OH:5])=[O:4].Cl.[CH3:15]O>>[CH3:15][O:4][C:3](=[O:5])[C@H:2]([OH:1])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].[OH:1][C@@H:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[C:3]([OH:5])=[O:4]Komponenten
Versuchsvorschrift
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.
Aufarbeitung
- customas described for the analogous reaction in scheme 2 (VIII→IX)
Quellen und Nachweise
- ORD-Eintrag
- ord-21685519b82e421db1859ac021a1e629
- Quelldatensatz
- uspto-grants-1996_03
- Patentnummer
- US05498786
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