Ethanolamine → N-((1S)-1-(benzylthiomethyl)-2-chloroethyl)-N-isobutylammonium chloride

Participants

Reaction Steps

(1S)-1-(Benzylthiomethyl)-2-hydroxyethylamine was made from (L)-S-benzylcysteine methyl ester as described in Method B1b. The 2-hydroxyethylamine was converted to (4S)-2-isopropyl-4-(benzylthiomethyl)-1,3-oxazolidine according to Method B4c, Step 1. The oxazolidine was reduced to N-((1S)-1-(benzylthiomethyl)-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-(benzylthiomethyl)-2-chloroethyl)-N-isobutylammonium chloride. 2-Ethyl-4-cyanophenyl isothiocyanate was reacted with N-((1S)-1-(benzylthiomethyl)-2-chloroethyl)-N-isobutylammonium chloride according to Method C1b to give (4S)-2-(2-ethyl-4-cyanophenylimino)-4-(benzylthiomethyl)-3-isobutyl-1,3-thiazolidine HCl salt.

Provenance & Evidence