1,5-Diazabicyclo(5,4,0)undec-5-ene → HCID 20526317, compound
Reaction equation
[CH2:1]([CH:8]1[C:14](=[O:15])[N:13]2[CH:9]1[CH2:10][C:11](Cl)([S:26]([CH2:28][CH3:29])=[O:27])[CH:12]2[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N12CCCCC1C=NCCC2>C(OCC)(=O)C>[CH2:1]([CH:8]1[C:14](=[O:15])[N:13]2[CH:9]1[CH2:10][C:11]([S:26]([CH2:28][CH3:29])=[O:27])=[C:12]2[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
4
Procedure
A solution of benzyl 6-benzyl-3-chloro-3-ethylsulphinyl-7-oxo-1-azabicyclo[3.2.0]heptane-2-carboxylate (79) (0.020 g) in ethyl acetate (2 ml) was treated with 1,5-diazabicyclo[5.4.0]undec-5-ene (0.0069 g). It was stirred for 15 mins. at room temperature and then the solution was washed with brine and dried over sodium sulphate. Concentration of the solution gave benzyl 6-benzyl-3-ethylsulphinyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (80) (0.016 g) as a colourless gum; νmax (CHCl3) 2990, 1790, 1725 and 1590 cm-1 ; λmax (ethanol) 308 nm; τ(CDCl3) 2.5-2.9 (10H, m, phenyls), 4.66 and 4.82 (2H, ABq J 12 Hz, OCH2), 5.99 (1H, ddd J 10, 8 and 3 Hz, C5-H), 6.39 (1H, ddd J 9 6 and 3 Hz, C6-H), 6.6-7.2 (4H, m, C4-H2 and C8-H2), 7.20 (2H, q J 71/2 Hz, SCH2) and 8.76 (3H, t J 71/2 Hz, CH3); (M+ at m/e 409.1333 C23H23NO4S requires 409.1348).