Реакция #10472

Уравнение реакции

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

Растворители

phosphate

DME

Условия реакции

Обработка

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

Методика

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).

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