FC(F)(F)C(O)=O.[C:8]([C@H:10]1[N:20]2[C@@H:14]([S:15][CH2:16][CH2:17][C@H:18]([NH:22]C(=O)OC(C)(C)C)[C:19]2=[O:21])[CH2:13][CH2:12][CH2:11]1)#[N:9]>C(Cl)Cl>[NH2:22][C@H:18]1[CH2:17][CH2:16][S:15][C@H:14]2[CH2:13][CH2:12][CH2:11][C@@H:10]([C:8]#[N:9])[N:20]2[C:19]1=[O:21]Trifluoroacetic acid (0.15 mL) was added to a 0° C. solution of tert-butyl (4S,7S,10aS)-7-cyano-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-ylcarbamate (36 mg, 0.11 mmol) in DCM (0.35 mL). The reaction mixture was then stirred at rt for 45 min. The reaction mixture was concentrated. The residue was partitioned between EtOAc and saturated aqueous NaHCO3. The EtOAc was isolated, dried over MgSO4, filtered and concentrated give (4S,7S,10aS)-4-amino-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carbonitrile (15 mg, 0.067 mmol, 60% yield).
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