C([C@@H](NS(C1C=CC(C)=CC=1)=O)[C@H](C)CC(F)(F)F)#N.[F:21][C:22]([F:32])([F:31])[CH2:23][C@@H:24]([CH3:30])[C@@H:25]([C:27]([OH:29])=[O:28])[NH2:26].[NH4+].[Cl-:34].C1(C)C(S(O)(=O)=O)=CC=CC=1>Cl>[ClH:34].[F:21][C:22]([F:31])([F:32])[CH2:23][C@@H:24]([CH3:30])[C@@H:25]([C:27]([OH:29])=[O:28])[NH2:26]A suspension of N-[(1S,2R)-1-cyano-4,4,4-trifluoro-2-methylbutyl]-4-methylbenzenesulfinamide (2.34 g, 7.69 mmol) in concentrated hydrochloric acid (75 mL) was heated to reflux for 18.5 h. After cooling to 25° C., the reaction mixture washed with diethyl ether several times. The aqueous layer was concentrated to give a mixture of 5,5,5-trifluoro-L-alloisoleucine, NH4Cl, and toluenesulfonic acid (2.35 g). The crude amino acid was used in the next step without further purification. Mass spectrum (−ESI): 309 (M−H)−.
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