[Cl:1]C1C=CC(C[C@H](N)CO)=CC=1.OCCN.[CH:17]([CH:20]1[NH:24][C@@H:23]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=2)[CH2:22]O1)([CH3:19])[CH3:18].O1CCNC1.[Cl:38]C1C=CC(C[C@H](NCC(C)C)CO)=CC=1.O=S(Cl)Cl>>[Cl-:1].[Cl:32][C:29]1[CH:30]=[CH:31][C:26]([CH2:25][C@H:23]([NH2+:24][CH2:20][CH:17]([CH3:19])[CH3:18])[CH2:22][Cl:38])=[CH:27][CH:28]=1(1S)-1-(4-Chlorophenylmethyl)-2-hydroxyethylamine was made from (L)-4-chlorophenylalanine methyl ester as described in Method B1b. The 2-hydroxyethylamine was converted to (4S)-2-isopropyl-4-(4-chlorophenylmethyl)-1,3-oxazolidine according to Method B4c, Step 1. The oxazolidine was reduced to N-((1S)-1-(4-chlorophenylmethyl)-2-hydroxyethyl)-N-isobutylamine according to Method B4c, Step 2. The resulting 2-Hydroxyethylamine was treated with SOCl2 according to Method B7c to give N-((1S)-1-(4-chlorophenylmethyl)-2-chloroethyl)-N-isobutylammonium chloride. 2-Ethyl-4-cyanophenyl isothiocyanate was reacted with N-((1S)-1-(4-chlorophenylmethyl)-2-chloroethyl)-N isobutylammonium chloride according to Method C1b to give (4S)-2-(2-ethyl-4-cyanophenylimino)-4-(4-chlorophenylmethyl)-3-isobutyl-1,3-thiazolidine HCl salt.
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