O[CH2:2][C@@H:3]([NH2:8])[CH:4]([CH3:7])[CH2:5][CH3:6].COC(=O)[C@H]([C@H](CC)C)N.OCCN.NC1C=CC=CC=1.[C:30]([C:32]1[CH:37]=[CH:36][C:35]([N:38]=[C:39]=[S:40])=[C:34]([CH3:41])[CH:33]=1)#[N:31]>>[C:30]([C:32]1[CH:37]=[CH:36][C:35]([NH2:38])=[C:34]([CH3:41])[CH:33]=1)#[N:31].[C:30]([C:32]1[CH:37]=[CH:36][C:35]([N:38]=[C:39]2[NH:8][C@@H:3]([CH:4]([CH2:5][CH3:6])[CH3:7])[CH2:2][S:40]2)=[C:34]([CH3:41])[CH:33]=1)#[N:31](1S)-1-(Hydroxymethyl)-2-methylbutylamine was made from (L)-isoleucine methyl ester as described in Method B1b. The 2-hydroxyethylamine was converted to (1S)-1-(chloromethyl)-2-methylbutanammonium chloride as described in Method B7a. 4-Cyano-2-methylaniline was synthesized as described in Method A1a. The aniline was converted to 4-cyano-2-methylphenyl isothiocyanate as described in Method A2a, Step 3. 4-Cyano-2-methylphenyl isothiocyanate was reacted with (1S)-1-(chloromethyl)-2-methylbutanammonium chloride to Method C1a to give (4S)-2-(4-cyano-2-methylphenylimino)-4-(2-butyl)-1,3-thiazolidine. The thiazolidine was reacted with isobutyl bromide according to Method D2a to give (4S)-2-(4-cyano-2-methylphenylimino)-4-butyl-3-isobutyl-1,3-thiazolidine.
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