Uses
Benzyl (
R)-(-)-mandelate can be employed as reactant to synthesize:
- (S)-α-Hydroxy-N-(2-phenylethyl)benzenepropanamide (α-hydroxyamides) by enzyme catalyzed amidation reaction.
- Optically pure (R)- monomethyl esters of 3-[(tert-butyldimethylsilyl)oxy]pentanedioic acid, which is employed in the preparation of HMG-CoA reductase inhibitors.
- O-Ibuprofenylmandelic acid via acylation reaction with optically active ibuprofen and subsequent hydrogenation.
- Benzyl (R)-2-fluoro-2-phenylacetate via deoxyfluorination of alcohols using AlkylFluor.
It can also be used to prepare HMG-CoA reductase inhibitors.
Synthesis
(1) Synthesis of benzyl (R)-2-hydroxy-2-phenylacetate (D-2): 85.1 g (559 mmol) of D-mandelic acid, 65 mL (628 mmol) of benzyl alcohol, and 1.01 g (5.35 mmol) of p-toluenesulfonic acid were dissolved in 700 mL of benzene, and the reaction was carried out at reflux for 6.5 hours. Upon completion of the reaction, the reaction mixture was washed with water and subsequently concentrated. The residue was recrystallized by ether to give 123.5 g (R)-benzyl 2-hydroxy-2-phenylacetate (D-2) in 91% yield. The melting point was 103.5°C-105°C. Elemental analysis (C15H14O3) Calculated values (%): C, 74.36; H, 5.82; Measured values (%): C, 74.53; H, 5.90. 1H-NMR (CDCl3-TMS) δ (ppm): 3.44 (d, J = 5.6 Hz, 1H), 5.14 (ABq, isolated, J = 12.3 Hz, 1H). J = 12.3 Hz, 1H), 5.22 (d, J = 5.6 Hz, 1H), 5.24 (ABq, Part B, J = 12.3 Hz, 1H), 7.15-7.50 (m, 10H). [α]D = -55.7 ± 1.0 (CHCl3, c = 1.003%, 24°C).
