[CH2:1]([O:3][C:4]([N:6]1[CH2:10][CH:9]2[CH:11]([C:15]([CH2:21][S:22]C(OCC)=S)(O)[C:16]([F:19])([F:18])[F:17])[C:12](=O)[CH2:13][CH:8]2[CH2:7]1)=[O:5])[CH3:2].Cl>C(Cl)Cl>[CH2:1]([O:3][C:4]([N:6]1[CH2:10][CH:9]2[C:11]3[C:15]([C:16]([F:19])([F:18])[F:17])=[CH:21][S:22][C:12]=3[CH2:13][CH:8]2[CH2:7]1)=[O:5])[CH3:2]Deoxygenated (N2 sparge for 15 min) N-methylpiperazine (1.3 ml) was placed in a 5 dram vial and cooled to 0° C. Next, a solution of 4-(1-Ethoxythiocarbonylsulfanylmethyl-2,2,2-trifluoro-1-hydroxy-ethyl)-5-oxo-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid ethyl ester (44 mg, 0.10 mmol) in CH2Cl2 (400 μl) was added dropwise over 15 minutes. After 3 hours, at 0° C., 12M HCl (10 ml) was added dropwise until pH 1-2 had been reached. The reaction was warmed to 22° C. and stirred for 1 hour. The reaction mixture was extracted with CH2Cl2 (3×20 ml) and H2O (30 ml). The organic layer was dried (MgSO4) and the crude oil was purified by flash chromatography (hexanes:EtOAc-7:3) providing the subtitle product as a clear oil (13.5 mg, 43%). 1H NMR (300 MHz, CDCl3, ppm) 1.24 (t, J=7 Hz, 3H); 2.78 (br d, J=16 Hz, 1H); 3.14 (dd, J1=16 Hz, J2=8 Hz, 1H); 3.20-3.38 (br m, 1H); 3.48-3.62 (br m, 2H); 3.63-3.88 (m, 3H); 4.11 (q, J=7 Hz, 2H); 7.59 (s, 1H).
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