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=C2C(=CC=1)C(=O)CC2.[O:34]=[C:35]1[C:43]2[C:38](=[CH:39][C:40]([N:44]=[C:45]=[S:46])=[CH:41][CH:42]=2)[CH2:37][CH2:36]1.[N-]=C=S>>[O:34]=[C:35]1[C:43]2[C:38](=[CH:39][C:40]([N:44]=[C:45]3[NH:8][C@@H:3]([CH:4]([CH2:5][CH3:6])[CH3:7])[CH2:2][S:46]3)=[CH:41][CH:42]=2)[CH2:37][CH2:36]1(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. 5-Aminoindan-1-one was converted to 1-oxo-5-indanyl isothiocyanate according to Method A2a. The isothiocyanate was reacted with (1S)-1-(chloromethyl)-2-methylbutanammonium chloride to Method C1a to give (4S)-2-(1-oxo-5-indanylimino)-4-(2-butyl)-1,3-thiazolidine. The thiazolidine was reacted with isobutyl bromide according to Method D2a to afford (4S)-2-(1-oxo-5-indanylimino)-4-(2-butyl)-3-isobutyl-1,3-thiazolidine.
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