Reaktion #363630

Reaktionsgleichung

(1S)-1-(Hydroxymethyl)-3-methylbutylamine

(L)-leucine methyl ester

2-Methyl-4-nitrophenyl isothiocyanate

2-hydroxyethylamine

→

(4S)-2-(2-methyl-4-nitrophenylimino)-4-isobutyl-1,3-thiazolidine

Reaktionsbedingungen

Vorschrift

(1S)-1-(Hydroxymethyl)-3-methylbutylamine was made from (L)-leucine methyl ester as described in Method B1b. The 2-hydroxyethylamine was converted to (1S)-1-(chloromethyl)-3-methylbutanammonium chloride as described in Method B7a. 2-Methyl-4-nitrophenyl isothiocyanate was reacted with (1S)-1-(chloromethyl)-3-methylbutanammonium chloride according to Method C1a to give (4S)-2-(2-methyl-4-nitrophenylimino)-4-isobutyl-1,3-thiazolidine. The thiazolidine was reacted with 2-chloro-3,3-dimethyl-2-butanone according to Method D2a to give (4S)-2-(2-methyl-4-nitrophenylimino)-4-isobutyl-3-(2-oxo-3,3-dimethyl-1-butyl)-1,3-thiazolidine. The ketone was reduced according to Method D5a to afford (4S)-2-(2-methyl-4-nitrophenylimino)-4-isobutyl-3-(3,3-dimethyl-2-hydroxy-1-butyl)-1,3-thiazolidine.

Quelle