C(Cl)(=O)C(Cl)=O.CS(C)=O.[S:11]([N:21]1[CH2:27][CH2:26][CH2:25][C@H:22]1[CH2:23][OH:24])([C:14]1[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=1)(=[O:13])=[O:12].C(N(CC)CC)C>C(Cl)Cl>[CH3:18][C:17]1[CH:19]=[CH:20][C:14]([S:11]([N:21]2[CH2:27][CH2:26][CH2:25][CH:22]2[CH:23]=[O:24])(=[O:13])=[O:12])=[CH:15][CH:16]=1To a stirred solution of 5 g (0.0394 mol) of oxalyl chloride in 50 ml of CH2Cl2 at -60° is added dropwise 7 g (0.0833 mol) of DMSO. The solution is stirred 30 minutes at -60° and then 10 g (0.039 mol) of N-tosylprolinol is added over five minutes at 60° and 15 ml of triethylamine is added. The solution is warmed to 25° and stirred one hour. The solution is then washed with H2O, dried over MgSO4 and the solvents removed. The residual oil, 10 g, is purified using a silica gel column and CHCl3 :MeOH (90:10) as the eluates. An oil is obtained which solidifies, 9.5 g (96%), mp 139°-140°.
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