Synthesis of a key intermediate, (S)-2-[(3-hydroxypropyl)sulfinyl]-1-(o-tolyl)imidazole, for the platelet aggregation inhibitor, OPC-29030 via lipase-catalyzed enantioselective transesterification

被引:36
作者
Morita, S
Matsubara, J
Otsubo, K
Kitano, K
Ohtani, T
Kawano, Y
Uchida, M
机构
[1] Tokushima Research Institute, Otsuka Pharmaceutical Co. Ltd., Tokushima 771-01, Kagasuno 463-10, Kawauchi-cho
关键词
D O I
10.1016/S0957-4166(97)00536-3
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Optically active 2-[(3-hydroxypropyl)sulfinyl]-1-(o-tolyl) (S)-2 was synthesized by kinetic resolution of (+/-)-2 with lipase and hydrolysis of the acetate (S)-3 with potassium carbonate. The reaction mixture of the lipase-catalyzed transesterification was converted to the phthalic acid derivative (R)-4, and this (R)-4 and the unreacted acetate (S)-3 were fractionated without use of column chromatography. The unrequired recovered alcohol (R)-2 was also racemized and (+/-)-2 was repeatedly submitted to the lipase-catalyzed transesterification. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:3707 / 3710
页数:4
相关论文
共 6 条
  • [1] HIGHLY ENANTIOSELECTIVE OXIDATION OF SULFIDES MEDIATED BY A CHIRAL TITANIUM COMPLEX
    BRUNEL, JM
    DITER, P
    DUETSCH, M
    KAGAN, HB
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (24) : 8086 - 8088
  • [2] A FACILE ROUTE TO HOMOCHIRAL SULFOXIDES
    BURGESS, K
    HENDERSON, I
    [J]. TETRAHEDRON LETTERS, 1989, 30 (28) : 3633 - 3636
  • [3] Furia F. D., 1984, SYNTHESIS-STUTTGART, P325
  • [4] NISHI T, 1995, Patent No. 733765
  • [5] ENZYMATIC HYDROLYZES OF THE SIGMA-SYMMETRICAL DICARBOXYLIC DIESTERS BEARING A SULFINYL GROUP AS THE PROCHIRAL CENTER
    TAMAI, S
    MIYAUCHI, S
    MORIZANE, C
    MIYAGI, K
    SHIMIZU, H
    KUME, M
    SANO, S
    SHIRO, M
    NAGAO, Y
    [J]. CHEMISTRY LETTERS, 1994, (12) : 2381 - 2384
  • [6] UNO T, 1995, CHEM PHARM BULL, V43, P1724