Methanol → (R)-methyl 2-hydroxydecanoate

Alternatively, the racemic hydroxyester (5.35 g, 26.5 mmol) can be dissolved in MeOH (24 mL) and H2O (56 mL) added. The enzyme was added (0.268 g, 5% by weight) and the pH adjusted by the addition of 1N NaOH. The reaction was stirred at ambient temperature for 55 hours by which time 15.0 mL of base had been added. Hexane (150 mL) was added in addition to Celite (2 g) and the reaction stirred for 0.25 hours. The reaction was filtered through Celite (6 g) and the filter washed with hexane (50 mL). The filter was washed with hexane (2×150 mL) and each of the hexane washes used to extract the aqueous methanol layer. The combined organic phase was washed with brine and dried (MgSO4) to obtain (R)-methyl 2-hydroxydecanoate (2.27 g, 0.011 mol, 43%): [α]D =-3.5° (c=1, MeOH).

1. additionThe enzyme was added (0.268 g, 5% by weight)
2. additionhad been added
3. filtrationThe reaction was filtered through Celite (6 g)
4. washthe filter washed with hexane (50 mL)
5. washThe filter was washed with hexane (2×150 mL)
6. extractionto extract the aqueous methanol layer
7. washThe combined organic phase was washed with brine
8. dry with materialdried (MgSO4)

ORD-Eintrag

ord-360dadc2abaa46edb0644e112c3f66e1

Quelldatensatz

uspto-grants-1996_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05498786