[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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