Expeditious synthesis of ramipril: An angiotensin converting enzyme (ACE) inhibitor

被引：5
作者：
Malakondaiah, Golla China [1 ]
Gurav, V. M. [1 ]
Reddy, Lekkala Amarnath
Babu, Karrothu Srihari
Bhaskar, Bolugoddu Vijaya
Reddy, Padi Pratap
Bhattacharya, Apurba
Anand, Ramasamy Vijaya
机构：
[1] Dr Reddys Labs Ltd, Ctr Excellence, IPDO, Bachupalli 500072, Andhra Pradesh, India
来源：
SYNTHETIC COMMUNICATIONS | 2008年 / 38卷 / 11期
关键词：
boric acid; esterification; L-(+)-mandelic acid; ramipril; resolution;
D O I：
10.1080/00397910801989238
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We document an efficient and cost-effective synthesis of ramipril 1 utilizing (i) an environmentally benign process for the esterification of racemic 2-aza-bicyclo-[3.3.0]-octane-3-carboxylic acid hydrochloride 2 using boric acid as a catalyst and (ii) a robust resolution process for the synthesis of 3a by means of inexpensive and recyclable L-(+)-mandelic acid as key steps.
引用
收藏
页码：1737 / 1744
页数：8
相关论文
共 26 条
  • [1] Ramipril: A review of its use in preventing cardiovascular outcomes in high-risk patients
    Anderson V.R.
    Perry C.M.
    Robinson D.M.
    [J]. American Journal of Cardiovascular Drugs, 2006, 6 (6) : 417 - 432
  • [2] [Anonymous], 2001, MERCK IND
  • [3] Babu P. R., 2005, Patent No. [PCT WO049568A1, 049568]
  • [4] Bankowski K., 2005, Patent No. [PCT WO108366A1, 108366]
  • [5] Bhaskar B. V., 2007, US Pat., Appl, Patent No. [11/696372, 11696372]
  • [6] Angiotensin-converting enzyme inhibitors and angiotensin receptor blockers in hypertension due to primary aldosteronism: A case for exclusion
    Bubbar, Carolyn D.
    Blackburn, David F.
    Wilson, Merne P.
    Wilson, Thomas W.
    [J]. ANNALS OF PHARMACOTHERAPY, 2007, 41 (01) : 129 - 132
  • [7] Gold E. H., 1986, [No title captured], Patent No. [US4587258, 4587258]
  • [8] Hock F., 1991, US Pat., Patent No. 5043346
  • [9] Green chemistry - a sustainable solution for industrial specialties applications
    Hoefer, Rainer
    Bigorra, Joaquim
    [J]. GREEN CHEMISTRY, 2007, 9 (03) : 203 - 212
  • [10] Boric acid catalyzed chemoselective esterification of α-hydroxycarboxylic acids
    Houston, TA
    Wilkinson, BL
    Blanchfield, JT
    [J]. ORGANIC LETTERS, 2004, 6 (05) : 679 - 681
123