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Volumn , Issue 5, 2000, Pages 448-449

A practical method for optical resolution of racemic alcohols or esters via lipase-catalyzed transformation and sulfation

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EID: 0034354383     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2000.448     Document Type: Article
Times cited : (20)

References (14)
  • 5
    • 0001889428 scopus 로고    scopus 로고
    • note
    • Preparation of (+)-methyl 2-acetyloxy-2-phenylacetate and (-)-methyl 2-hydroxy-2-phenylacetate was performed as follows: A suspension of lipase (LIP, Toyobo Co. Ltd.) 1.50 g, (±)-methyl 2-hydroxy-2-phenylacetate 1.00 g, Molecular sieves 4A 5.0 g, and vinyl acetate 3.0 ml in diisopropyl ether 100 ml was stirred at 35 °C for 3 h. After the lipase was removed by filtration, the filtrate was concentrated under reduced pressure to give a residue containing methyl (S)-(+)-2-(acetyloxy)-2-phenylacetate (93% ee) and methyl (R)-(-)-2-hydroxy-2-phenylacetate (99% ee). The residue was dissolved in pyridine 10 ml and DMF 2 ml, and to this solution sulfur trioxide pyridine complex 1.95 g was added. After stirring at room temperature for 1 h, diisopropyl ether 70 ml was added. The mixture was washed with successive water, dilute hydrochloric acid and brine, then dried over sodium sulfate. The filtrate was concentrated under reduced pressure to afford methyl (S)-(+)-2-(acetyloxy)-2-phenylacetate 0.559 g (45%, 92% ee) as an oil. The combined aqueous layers were concentrated and treated with 10% methanolic hydrochloric acid. A similar work up afforded methyl (R)-(-)-2-hydroxy-2-phenylacetate 0.341 g (34%, 96% ee).
  • 6
    • 0001930203 scopus 로고    scopus 로고
    • note
    • The acetate was hydrolyzed to give an alcohol, which was subjected to HPLC analysis. Column: CHIRALCEL OD (Daicel Chemical Industries, Ltd.), Mobile phase: hexane/2-propanol (97/3), Flow rate: 1.0 ml/min, Detection: UV (280 nm), Temperature: room temperature.
  • 7
    • 0001728925 scopus 로고    scopus 로고
    • note
    • Column: CHIRALCEL OD (Daicel Chemical Industries Ltd.), Mobile phase: hexane/2-propanol (99/1), Flow rate: 1.2 ml/min. Detection: UV (254 nm), Temperature: room temperature.
  • 8
    • 0001928371 scopus 로고    scopus 로고
    • note
    • Column: CHIRALCEL OJ (Daicel Chemical Industries, Ltd.), Mobile phase: hexane/2-propanol (98/2), Flow rate: 1.2 ml/min, Detection: UV (220 nm), Temperature: room temperature.
  • 9
    • 0001801229 scopus 로고    scopus 로고
    • note
    • Column: CHIRALCEL OB (Daicel Chemical Industries, Ltd.), Mobile phase: hexane/2-propanol (1000/5), Flow rate: 1.0 ml/min. Detection: UV (254 nm), Temperature: room temperature.
  • 10
    • 0001936765 scopus 로고    scopus 로고
    • note
    • Column: CHIRALCEL OD two pieces (Daicel Chemical Industries, Ltd.), Mobile phase: hexane/2-propanol (1000/5), Flow rate: 1.0 ml/min, Detection: UV (254 nm), Temperature: room temperature.
  • 11
    • 0001705987 scopus 로고    scopus 로고
    • note
    • (GLC) Column: Chirasil Dex-CB (25 m × 0.25 mm I.D., Chrompack), Oven temperature: 80 °C ∼ 150 °C, Injection temperature: 200 °C, Detection temperature: 200 °C, Carrier gas: Helium.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.