Citation: Hui-Jiao Wen, Qing Chen, Guo-Jun Zheng. Enantioselective synthesis of (1S,4R)-N-(benzylcarbamoyl)-4-aminocyclopent-2-en-1-ol by Candida antarctica lipase B[J]. Chinese Chemical Letters, ;2015, 26(11): 1431-1434. doi: 10.1016/j.cclet.2015.07.005 shu

Enantioselective synthesis of (1S,4R)-N-(benzylcarbamoyl)-4-aminocyclopent-2-en-1-ol by Candida antarctica lipase B

1.
State Key Laboratory of Chemical Resources Engineering, Beijing University of Chemical Technology, Beijing 100029, China

Corresponding author: Guo-Jun Zheng,
Received Date: 15 April 2015
Available Online: 24 June 2015

An efficient biocatalytic process has been developed to obtain optically pure (1S,4R)-N-(benzylcarbamoyl)- 4-aminocyclopent-2-en-1-ol which can be used as the key intermediate of ticagrelor. In this research, several N-(benzylcarbamoyl)-4-aminocyclopent-2-en-1-ol derivatives have been investigated in which Candida antarctica lipase B (CALB) was used to catalyze the asymmetric hydrolysis reaction. As expected, some of these substrates successfully gave (1S,4R)-N-(benzylcarbamoyl)-4-aminocyclopent- 2-en-1-ol in >98% enantiomeric excess (ee) with conversion yields up to 45%.
- N-(Benzylcarbamoyl)-4-aminocyclopent-2-
1. [1]
  [1] F. Burlina, A. Favre, J.L. Fourrey, M. Thomas, An expeditious route to carbocyclic nucleosides: (61)-aristeromycin and (61)-carbodine, Bioorg. Med. Chem. Lett. 7 (1997) 247-250.
2. [2]
  [2] K.H. Park, H. Rapoport, Enantioselective synthesis of (1R,4S)-1-amino-4-(hydroxymethyl)- 2-cyclopentene, a precursor for carbocyclic nucleoside synthesis, J. Org. Chem. 59 (1994) 394-399.
3. [3]
  [3] B.M. Trost, D. Stenkamp, S.R. Pulley, An enantioselective synthesis of cis-4-tertbutoxycarbamoyl- 1-methoxycarbonyl-2-cyclopentene—a useful, general building block, Chem. A: Eur. J. 1 (1995) 568-572.
4. [4]
  [4] T. Ando, K. Kojima, P. Chahota, et al., Synthesis of 4'-modified noraristeromycins to clarify the effect of the 4'-hydroxyl groups for inhibitory activity against S-adenosyl-L-homocysteine hydrolase, Bioorg. Med. Chem. Lett. 18 (2008) 2615-2618.
5. [5]
  [5] N.G. Ramesh, A.J. Klunder, B. Zwanenburg, Enantioselective synthesis of 4-acetylaminocyclopent- 2-en-1-ols from tricyclo[5.2.1.0(2, 6)]decenyl enaminones. Precursors for 5'-norcarbocyclic nucleosides and related antiviral compounds, J. Org. Chem. 64 (1999) 3635-3641.
6. [6]
  [6] P.F. Vogt, J.G. Hansel, M.J. Miller, Asymmetric synthesis of an important precursor to 5'-nor carbocyclic nucleosides, Tetrahedron Lett. 38 (1997) 2803-2804.
7. [7]
  [7] D. Zhang, A. Ghosh, C. Suling, et al., Efficient functionalization of acylnitroso cycloadducts: application to the syntheses of carbocyclic nucleoside precursors, Tetrahedron Lett. 37 (1996) 3799-3802.
8. [8]
  [8] J.J.J. Van Giezen, L. Nilsson, P. Berntsson, et al., Ticagrelor binds to human P₂Y (12) independently from ADP but antagonizes ADP-induced receptor signaling and platelet aggregation, J. Thromb. Haemostasis. 7 (2009) 1556-1565.
9. [9]
  [9] B. Springthorpe, A. Bailey, P. Barton, From ATP to AZD6140: the discovery of an orally active reversible P2Y12 receptor antagonist for the prevention of thrombosis, Bioorg. Med. Chem. Lett. 17 (2007) 6013-6018.
10. [10]
  [10] M. Arita, K. Adachi, Y. Ito, et al., Enantioselective synthesis of the carbocyclic nucleosides (-)-aristeromycin and (-)-neplanocin A by a chemicoenzymatic approach, J. Am. Chem. Soc. 105 (1983) 4049-4055.
11. [11]
  [11] M. Ikbal, C. Cerceau, F. Le Goffic, et al., Synthè se des deux énantiomè res de l'analogue carbocyclique du nicotinamide ribose et évaluation de leurs proprié té s biologiques, Eur. J. Med. Chem. 24 (1989) 415-420.
12. [12]
  [12] S. Saul, S. Corr, J. Micklefield, Biotransformations in low-boiling hydrofluorocarbon solvents, Angew. Chem. Int. Ed. 43 (2004) 5519-5523.
13. [13]
  [13] J. Dauvergne, A.M. Happe, V. Jadhav, et al., Synthesis of 4-azacyclopent-2-enones and 5,5-dialkyl-4-azacyclopent-2-enones, Tetrahedron 60 (2004) 2559-2567.
14. [14]
  [14] C.R. Johnson, S.J. Bis, Enzymatic asymmetrization of meso-2-cycloalken-1 4-diols and their diacetates in organic and aqueous media, Tetrahedron Lett. 33 (1992) 7287-7290.
15. [15]
  [15] D. Zhang, M.J. Miller, Total synthesis of (±) carbocyclic polyoxin C and its α-epimer, J. Org. Chem. 63 (1998) 755-759.
16. [16]
  [16] M.J. Mulvihill, J.L. Gage, M.J. Miller, Enzymatic resolution of aminocyclopentenols as precursors to D-and L-carbocyclic nucleosides, J. Org. Chem. 63 (1998) 3357-3363.
17. [17]
  [17] E.M. Anderson, K.M. Larsson, O. Kirk, One biocatalyst - many applications: the use of Candida antarctica B-lipase in organic synthesis, Biocatal. Biotransform. 16 (1998) 181-204.
18. [18]
  [18] L. Bollans, J. Bacsa, J.A. Iggo, et al., The acyl nitroso Diels-Alder (ANDA) reaction of sorbate derivatives: an X-ray and 15N NMR study with an application to aminoacid synthesis, Org. Biomol. Chem. 7 (2009) 4531-4538.
19. [19]
  [19] Compound 2: ¹H NMR (400 MHz, CDCl₃): δ 7.47-7.09 (m, 5H), 5.97 (m, 2H), 5.55 (s, 1H), 5.11 (s, 2H), 4.85 (m, 1H), 4.76 (m, 1H), 2.84 (m, 1H), 2.30 (t, 2H), 1.56 (m, 1H), 1.17 (t, 3H). Compound 3: ¹H NMR (400 MHz, CDCl3): d 7.61-7.24 (m, 5H), 5.98 (m, 2H), 5.55 (s, 1H), 5.11 (s, 2H), 4.83 (m, 1H), 4.69 (m, 1H), 2.97-2.65 (m, 1H), 2.29 (t, 2H), 1.70-1.48 (m, 3H), 0.98 (t, 3H). Compound 4: ¹H NMR (400 MHz, CDCl3): δ 7.94-7.13 (m, 10H), 6.01 (m, 2H), 5.72 (s, 1H), 5.11 (s, 2H), 4.85(m, 1H), 4.75 (m, 1H), 2.97-2.85 (m, 1H), 1.65 (m, 1H).
20. [20]
  [20] L. Werner, J.R. Hudlicky, M. Wernerova, et al., Synthesis of 1,2-and 1,4-amino alcohols from 1,3-dienes via oxazines. Rearrangements of 1,4-amino alcohol derivatives to oxazolines, Tetrahedron 66 (2010) 3761-3769.
21. [21]
  [21] Analytical HPLC methods: the enantiomeric excess analysis was performed using a HPLC system (Shimadzu, Japan) equipped with a CHIRALPAK IF column (0.46 mm × 250 mm × 5 mm), elution with ethanol/hexane 15:85 v/v for compound 1, ethanol/hexane 25:75 v/v for compounds 2 and 3, ethanol/hexane 30:70 for compound 4.
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