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 250C, the reaction mixture was 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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