[Cl:1][CH2:2][C:3](Cl)=[O:4].ClCCl.Cl.[NH:10]1[CH2:17][S:16][CH2:15][C@H:11]1[C:12]([NH2:14])=[O:13].FC(F)(F)C(OC(=O)C(F)(F)F)=O>N1C=CC=CC=1.C(N(CC)CC)C>[ClH:1].[NH:10]1[CH2:17][S:16][CH2:15][C@H:11]1[C:12]([NH2:14])=[O:13].[Cl:1][CH2:2][C:3]([N:10]1[C@H:11]([C:12]#[N:14])[CH2:15][S:16][CH2:17]1)=[O:4]L-thioprolineamide hydrochloride was synthesized according to the process described in the literature. (Ashworth et. al., Bioorg. Med. Chem. Lett., Vol. 6, pp. 2745-2748, 1996). 2.36 ml of chloroacetyl chloride was added to 150 ml of a dichloromethane solution containing 5.00 g of the thus obtained L-thioprolineamide hydrochloride and 8.67 ml of triethylamine under ice-cooling, and the mixture was stirred at the same temperature for 1 hour. To the reaction-mixture were added 4.8 ml of pyridine and 8.4 ml of trifluoroacetic anhydride, and the mixture was further stirred at room temperature for 1 hour. The reaction mixture was washed with an aqueous 10% HCl solution and water, dried over magnesium sulfate, filtered and concentrated under reduced pressure. Subsequently, the residue was crystallized from ether to obtain 4.82 g of (R)-3-chloroacetyl-4-cyanothiazolidine as a yellowish brown crystal.
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