Hexahydro-Pyrrolo[1,2,5:3,4,5]Thiazolo[3,4-c]Oxazol-1-ones: New Chiral Tricyclic L-Cysteine and D-Penicillamine Derivatives

Teresa M.V.D. Pinho e Melo, Susana M.M. Lopes, Antonio M. d'A. Rocha Gonsalves, Agnieszka Kaczor, Rui Fausto, Jose Paixao, Ana Matos Beja, Manuela Ramos Silva
2006 Letters in Organic Chemistry  
A simple and efficient approach to the synthesis of the new chiral hexahydropyrrolo [1',2',5':3,4,5]thiazolo [3,4-c]oxazol-1-one ring system is reported. Infrared spectroscopy, quantum-chemical calculations and X-ray analysis allowed the stereochemistry assignment of (2aS,4aR,6aR)-2a,3,4,4a,6,6ahexahydropyrrolo-[1',2',5':3,4,5]thiazolo[3,4-c]oxazol-1-one. (2aS,4aR,6aR)-2a,3,4,4a,6,6a-hexahydropyrrolo-[1', 2',5':3,4,5]thiazolo[3,4-c]oxazol-1-one 4. Mp 99.3-100.2 ºC (from ethyl acetate/hexane)
more » ... acetate/hexane) (Found: C, 49.0; H, 5.0; N, 8.2. C 7 H 9 NO 2 S requires C, 49.1; H, 5.3; N, 8.2%). ν (KBr) 1724 and 1225 cm -1 . H 2.44-2.32 (2H, m), 2.42-2.48 (2H, m), 3,45 (1H, dd, J = 5.9 and 12.2 Hz), 3.56 (1H, approx. d, J = 12.2 Hz), 4.12 (1H, approx. d, J = 5.9 Hz), 4.93 (1H, dd, J = 2.8 and 6.0 Hz), 5.55 (1H, dd, J = 2.0 and 5.0 Hz); C 27.2, 31.4, 39.2, 67.1, 74.9, 98.4; m/z 127 [(M + -CO 2 ), 10%], 93 (100) and 65 (29). HRMS (CI+) m/z 172.0430 (C 7 H 9 NO 2 S [MH + ], requires 172.0432). [α] 25 D = + 30 (c = 1.0, CH 2 Cl 2 ).
doi:10.2174/157017806779116996 fatcat:sbmayaucqzhgvghvnxlvu3vzj4