Cl.[N:2]12[CH2:10][C:6]([C:11]([OH:13])=[O:12])([CH2:7][CH2:8][CH2:9]1)[CH2:5][CH2:4][CH2:3]2.S(Cl)(Cl)=O.[C:18](=[N:21][OH:22])([NH2:20])[CH3:19].[C:23](=[O:26])([O-:25])[O-].[K+].[K+]>C(Cl)(Cl)Cl.O.C1(C)C(C)=CC=CC=1>[C:11]([OH:13])(=[O:12])[C:23]([OH:25])=[O:26].[CH3:19][C:18]1[N:20]=[C:11]([C:6]23[CH2:10][N:2]([CH2:9][CH2:8][CH2:7]2)[CH2:3][CH2:4][CH2:5]3)[O:22][N:21]=11-Azabicyclo[3.3.1]non-5-ylcarboxylic acid hydrochloride salt (D14) (1.79 g, 0.0087 mole) was treated with thionyl chloride (20 ml) and heated under reflux for 5 h. The solution was concentrated in vacuo to leave a white solid, which was taken up in chloroform (150 ml), treated with acetamide oxime (D17) (770mg, 0.0104 mole) and heated under reflux for 6 h. The reaction mixture was basified with saturated potassium carbonate solution and extracted with chloroform (3×80 ml). The combined extracts were dried (Na2SO4) and concentrated to leave a white solid, which was treated with xylene (200 ml) and heated under reflux for 1.5 h, using a Dean and Stark head to trap water formed. The reaction mixture was concentrated in vacuo to leave a yellow oil, which was chromatographed on silica gel eluting with 5% methanol/chloroform to give a colourless oil (1.60 g, 89%). This was converted to the oxalate salt and recrystallised from ethanol/ether to give the title compound (E9) as a white solid m.p. 168°-170° C.
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