반응 #10472

반응 방정식

acetic anhydride

3-[2-(4-fluorophenyl)oxazol-4-ylmethoxyl]cyclohexyl acetate

mono(3-benzyloxycyclohexyl) glutarate

3-benzyloxycyclohexan-1-ol

→

(1R,3S)-3-[2-(4-fluorophenyl)oxazol4-ylmethoxy]cyclohexan-1-ol

용매

phosphate

DME

반응 조건

후처리

1. 1
   workup.WAIT, at 20–23° C. for approx. 20–24 h
2. 2
   추출The reaction mixture was extracted with dichloromethane
3. 3
   농축concentrated by evaporation under reduced pressure

실험 절차

Approx. 10 mg of 3-[2-(4-fluorophenyl)oxazol-4-ylmethoxyl]cyclohexyl acetate (prepared by reacting 3-benzyloxycyclohexan-1-ol with acetic anhydride, in a similar manner to the synthesis of mono(3-benzyloxycyclohexyl) glutarate see Example 39) were taken up in 2 ml of phosphate buffer (0.1 M, pH=7.0) and 2 ml of DME and stirred with approx. 5 mg of Chirazyme L-2, lyo., at 20–23° C. for approx. 20–24 h. The reaction mixture was extracted with dichloromethane. The organic phase was admixed with toluene and concentrated by evaporation under reduced pressure. The determination of the optical purity for (1R,3S)-3-[2-(4-fluorophenyl)oxazol4-ylmethoxy]cyclohexan-1-ol gave 99.4% ee (HPLC on Chiralpak AD 250×4.6; 1 ml/min, acetonitrile) and 98.9% ee for the (1S,3R)-acetate (HPLC on Chiralcel OD 250×4.6; 1 ml/min, 110:5:1 heptane/EtOH/CH3CN+0.1% TFA).

출처