Syntheses of dipeptides containing (1R,5S)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2(S)-carboxylic acid (4), (1R,5S)-spiro[3-azabicyclo[3.1.0]hexane-6,1′-cyclopropane]- 2(S)-carboxylic acid (5) and (1S,5R)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2(S)-carboxylic acid (6)

Tetrahedron Letters

Volumn 47, Issue 36, 2006, Pages 6469-6472

  Hendrata, Siska ^a   Bennett, Frank ^a   Huang, Yuhua ^a   Sannigrahi, Mousumi ^a   Pinto, Patrick A ^a   Chan, Tze Ming ^a   Anderson Evans, C ^a   Osterman, Rebecca ^a   Buevich, Alexei ^a   McPhail, Andrew T ^b  

^a MERCK RESEARCH LABORATORIES   (United States)

^b DUKE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

6,6 DIMETHYL 3 AZABICYCLO[3.1.0]HEXANE 2 CARBOXYLIC ACID; CARBOXYLIC ACID DERIVATIVE; DIPEPTIDE; ENZYME INHIBITOR; HEXANE; SPIRO[3 AZABICYCLO[3.1.0]HEXANE 6,1' CYCLOPROPANE] 2 CARBOXYLIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; PEPTIDE SYNTHESIS;

EID: 33746604295     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.06.052     Document Type: Article

References (19)

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15. 2 (0.317 g; 1.4 mmol) was added and the resulting orange solution was heated to 70 °C, under an atmosphere of nitrogen, for 1.5 h. After cooling, the benzene was removed under reduced pressure and the crude brown reaction product was purified by silica gel column chromatography using EtOAc/hexanes (1:5) as eluent providing the exo-type cycloadduct 14 (1.94 g; 35%), as a light-yellow solid followed by the endo-isomer 15 (1.97 g; 36%).
16. Crystallographic data for lactam 16 have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication No. CCDC 607122. Copies of the data can be obtained, free of charge, on application to the Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44-(0)1223-336033 or e-mail: deposit@ccdc.cam.ac.uk).
17. 3) δ 173.9 (C-10), 172.0 (C-9), 155.8 (C-13), 79.9 (C-14), 61.3 (C-2), 58.4 (C-11), 49.7 (C-5), 35.5 (C-16), 30.3 (C-3), 28.3 (C-15), 26.8 (C-4), 26.5 (C-7), 26.2 (C-17), 20.7 (C-6), 14.5 (C-8).{A figure is presented}
18. 3) δ 173.2 (C-10), 174.0 (C-9), 155.9 (C-13), 79.8 (C-14), 60.0 (C-2), 58.7 (C-11), 49.0 (C-5), 35.1 (C-16), 28.3 (C-15), 26.3 (C-17), 23.2 (C-3), 21.0 (C-4), 16.3 (C-6), 6.6 (C-7), 0.7 (C-8).
19. 3) δ 174.1 (C-10), 172.3 (C-9), 156.0 (C-13), 79.8 (C-14), 59.5 (C-2), 58.7 (C-11), 48.1 (C-5), 35.0 (C-16), 29.7 (C-3), 28.2 (C-15), 27.3 (C-4), 26.22 (C-17), 26.19 (C-7), 19.3 (C-6), 12.4 (C-8).