Reaktion #363636

ord-c78b179939f44bd394fca26ad903493f

Reaktionsgleichung

CC(C)C[C@H](N)CO
(1S)-1-(Hydroxymethyl)-3-methylbutylamine
COC(=O)[C@@H](N)CC(C)C
(L)-leucine methyl ester
Cc1cc(C#N)cc(Cl)c1N=C=S
2-Chloro-4-cyano-6-methylphenyl isothiocyanate
NCCO
2-hydroxyethylamine
Cc1cc(C#N)cc(Cl)c1N=C1N[C@@H](CC(C)C)CS1
(4S)-2-(2-chloro4-cyano-6-methylphenylimino)-4-isobutyl-1,3-thiazolidine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

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-Chloro-4-cyano-6-methylphenyl isothiocyanate was reacted with (1S)-1-(chloromethyl)-3-methylbutanammonium chloride according to Method C1c to give (4S)-2-(2-chloro4-cyano-6-methylphenylimino)-4-isobutyl-1,3-thiazolidine. The thiazolidine was reacted with isobutyl bromide according to Method D2f to afford (4S)-2-(2-chloro-4-cyano-6-methylphenylimino)-3,4-diisobutyl-1,3-thiazolidine trifluoroacetate salt.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06353006B1uspto-grants-2002_03