(Z)-5-(4-fluorophenyl)pent-4-enoic acid: A precursor for convenient and efficient synthesis of the antihypercholesterolemia agent ezetimibe

Synthesis

Volumn , Issue 20, 2010, Pages 3433-3438

  Sova, Matej ^a   Mravljak, Janez ^a   Kovač, Andreja ^a   Pečar, Slavko ^a,c   Časar, Zdenko ^b   Gobec, Stanislav ^a  

^a UNIVERSITY OF LJUBLJANA   (Slovenia)

^b Lek Pharmaceuticals dd a Sandoz company   (Slovenia)

^c JO EF STEFAN INSTITUTE   (Slovenia)

Author keywords

(Z) 5 (4 fluorophenyl)pent 4 enoic acid; asymmetric synthesis; azetidinone; cholesterol absorption inhibitor; Wittig reaction

Indexed keywords

(Z)-5-(4-FLUOROPHENYL)PENT-4-ENOIC ACID; ASYMMETRIC SYNTHESIS; AZETIDINONE; CHOLESTEROL ABSORPTION INHIBITOR; WITTIG REACTION;

ABSORPTION; ACIDS; CHOLESTEROL;

SYNTHESIS (CHEMICAL);

3 [2 [[4 (BENZYLOXY)PHENYL](4 FLUOROPHENYLAMINO)METHYL] 5 (4 FLUOROPHENYL)PENT 4 ENOYL] 4 PHENYLOXAZOLIDIN 2 ONE; 3 [5 (4 FLUOROPHENYL)PENT 4 ENOYL] 4 PHENYLOXAZOLIDIN 2 ONE; 4 [4 (BENZYLOXY)PHENYL] 1 (4 FLUOROPHENYL) 3 [ (4 FLUOROPHENYL)ALLYL]AZETIDIN 2 ONE; 4 [4 (BENZYLOXY)PHENYL] 1 (4 FLUOROPHENYL) 3 [3 (4 FLUOROPHENYL) 3 HYDROXYPROPYL]AZETIDIN 2 ONE; 4 [4 (BENZYLOXY)PHENYL] 1 (4 FLUOROPHENYL) 3 [3 (4 FLUOROPHENYL) 3 OXOPROPYL]AZETIDIN 2 ONE; 5 (4 FLUOROPHENYL)PENT 4 ENOIC ACID; ETHYL 5 (4 FLUOROPHENYL)PENT 4 ENOATE; ETHYL 5 (4 FLUOROPHENYL)PENT 4 ENOIC ACID; EZETIMIBE; UNCLASSIFIED DRUG; VALERIC ACID;

ARTICLE; CHEMICAL REACTION; CHIRALITY; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; HYPERCHOLESTEROLEMIA; NUCLEAR MAGNETIC RESONANCE; PURIFICATION; STEREOCHEMISTRY; WITTIG REACTION;

EID: 77957809858     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1258193     Document Type: Article

References (60)

1. Knopp R H., Gitter H, Truitt T, Bays H, Manion C V., Lipka L J., LeBeaut A P., Suresh R, Yang B, Veltri E P., Eur. Heart J. 2003 24 729
2. Bays H E., Moore P B., Drehobl M A., Rosenblatt S, Toth P D., Dujovne C A., Knopp R H., Lipka L J., LeBeaut A P., Yang B, Mellars L E., Cuffie-Jackson C, Veltri E P., Clin. Ther. 2001 23 1209
3. Rosenblum S B., In The Art of Drug Synthesis Johnson D J. Li J J. Wiley-Interscience New Jersey 2007 183-196; and references cited therein
4. Shankar B B., US Patent 5856473 1999
5. Chem. Abstr. 1999, 130, 110148
6. Thiruvengadam T K., Sudhakar A R., Wu G, In Process Chemistry in the Pharmaceutical Industry Gadamasetti K G. Marcel Dekker New York 1999 221-242; and references cited therein
7. Burnett D A., Caplen M A., Domalski M S., Browne M E., Davis H R. Jr., Clader J W., Bioorg. Med. Chem. Lett. 2002 12 311
8. Xu X, Fu R, Chen J, Chen S, Bai X, Bioorg. Med. Chem. Lett. 2007 17 101
9. (a) Sawant, M. S.; Pillai, B. K. G.; Bhirud, S. B.; Sharma, K. PCT Int. Appl. WO 2007017705, 2007;
10. Chem. Abstr. 2007, 146, 229083.
11. (b) Escude, A. G. I.; Llado, J. B. I.; Nettekoven, U. PCT Int. Appl. WO 2007144780, 2007;
12. Chem. Abstr. 2007, 148, 78871.
13. (c) Kansal, K. K.; Ahmad, S.; Mariappan, S.; Tyagi, B.; Perlman, N.; Le Paih, J.; Zanotti-Gerosa, A. PCT Int. Appl. WO 2007120824, 2007;
14. Chem. Abstr. 2007, 147, 486269.
15. (d) Bodi, J.; Eles, J.; Szoeke, K.; Vukics, K.; Gati, T.; Temesvari, K.; Kiss- Bartos, D. PCT Int. Appl. WO 2007072088, 2007;
16. Chem. Abstr. 2007, 147, 95527.
17. (e) Ramakrishnan, A.; Shrigadi, N. B.; Prabhavalkar, T. S.; Thorat, A. N. PCT Int. Appl. WO 2007108007, 2007;
18. Chem. Abstr. 2007, 147, 385762.
19. (f) Uppala, V. B. R.; Vaddadi, P. R.; Sunkara, V. V.; Cheemalapati, V. A. S.; Padaga, K. S. K. US Pat. Appl. Publ. US 2007049748, 2007;
20. Chem. Abstr. 2007, 146, 295763.
21. (g) Perlman, N.; Fishman, A. PCT Int. Appl. WO 2008151324, 2008;
22. Chem. Abstr. 2008, 150, 19943.
23. (h) Srinivasan, C. V.; Saxena, R.; Gupta, P.; Wadhwa, L. PCT Int. Appl. WO2008096372, 2008;
24. Chem. Abstr. 2008, 149, 267891.
25. (i) Slavikova, M.; Vesilek, P.; Obadalova, I.; Hajicek, J. PCT Int. Appl. WO 2008106900, 2008;
26. Chem. Abstr. 2008, 149, 355683.
27. (j) Allegrini, P.; Naldini, D.; Razzetti, G.; Taddei, M. Ital. Appl. IT 2007MI2013, 2008;
28. Chem. Abstr. 2008, 152, 168785.
29. (k) Štimac, A.; Mohar, B.; Stephan, M.; Bevc, M.; Zupet, R.; Gartner, A.; Krošelj, V.; Smrkolj, M. Eur. Pat. Appl. EP 1953140, 2008;
30. Chem. Abstr. 2008, 149, 224075.
31. (l) Satyanarayana Reddy, M.; Sahadeva Reddy, M. PCT Int. Appl. WO 2008032338, 2008;
32. Chem. Abstr. 2008, 148, 355561.
33. (m) Szabo, L.; Toth, L.; Perlman, N. PCT Int. Appl. WO 2009032264, 2009;
34. Chem. Abstr. 2009, 150, 304851.
35. (n) Stepankova, H.; Hajicek, J.; Slavikova, M.; Zezula, J. PCT Int. Appl. WO 2009106021, 2009;
36. Chem. Abstr. 2009, 151, 313529.
37. (o) Huang, Z.; Dai, L.; Han, Y. Chin. Pat. Appl. CN 101423511, 2009;
38. Chem. Abstr. 2009, 151, 8510.
39. (p) Venkateswaran, S. C.; Gurdeep, S. S.; Gupta, P.; Wadhwa, L. PCT Int. Appl. WO 2009157019, 2009;
40. Chem. Abstr. 2009, 152, 97325.
41. (q) Du, H.; Zheng, L.; Chen, X. Chin. Pat. Appl. CN 101423515, 2009;
42. Chem. Abstr. 2009, 150, 563526.
43. (r) Slavikova, M.; Stepankova, H.; Zezula, J.; Hajlcek, J. PCT Int. Appl. WO 2009140932, 2009;
44. Chem. Abstr. 2009, 152, 12131.
45. (s) Stepankova, H.; Hajicek, J.; Slavikova, M.; Zezula, J. PCT Int. Appl. WO 2009067960, 2009;
46. Chem. Abstr. 2009, 151, 33290.
47. (t) Selič, L. PCT Int. Appl. WO 2009150038, 2009;
48. Chem. Abstr. 2009, 152, 62067.
49. (u) Reddy, R. B.; Reddy, G. M.; Sahadev, K.; Nagaraju, M. Indian Pat. Appl. IN 2007CH02953, 2009.
50. Sasikala C H. V. A., Padi P R., Sunkara V, Ramayya P, Dubey P K., Uppala V B. R., Praveen C, Org. Process Res. Dev. 2009 13 907
51. Rosenblum S B., Huynh T, Afonso A, Davis H R. Jr., Tetrahedron 2000 56 5735
52. Lamb R C., Spadafino L P., Webb R G., Smith E B., McNew W E., Pacifici J G., J. Org. Chem. 1966 31 147
53. Murakami M, Ishida N, Miura T, Chem. Commun. 2006 643
54. Lemhadri M L., Battace A, Zair T, Doucet H, Santelli M, J. Organomet. Chem. 2007 692 2270
55. Mravljak J, Sova M, Kova A, Gobec S, asar Z, PCT Int. Appl. WO 2010012775 2010;
56. Chem. Abstr. 2010, 152, 215003
57. Tsuji J, Synthesis 1984 369
58. Miller D G., Wayner D D. M., J. Org. Chem. 1990 55 2924
59. Rosenblum S B., Huynh T, Afonso A, Davis H R., Yumibe N, Clader J W., Burnett D, J. Med. Chem. 1998 41 973
60. Wu G, Wong Y, Chen X, Ding Z, J. Org. Chem. 1999 64 3714