Reaktion #363635

ord-78e0a9f0ed654e6aab9187da4be70f17

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
N#Cc1ccc(N=C=S)c(C(F)(F)F)c1
4-Cyano-2-(trifluoromethyl)phenyl isothiocyanate
NCCO
2-hydroxyethylamine
CC(C)C[C@H]1CSC(=Nc2ccc(C#N)cc2C(F)(F)F)N1
(4S)-2-(4-cyano-2-(trifluoromethyl)phenylimino)-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. 4-Cyano-2-(trifluoromethyl)phenyl isothiocyanate was reacted with (1S)-1-(chloromethyl)-3-methylbutanammonium chloride according to Method C1c to give (4S)-2-(4-cyano-2-(trifluoromethyl)phenylimino)-4-isobutyl-1,3-thiazolidine. The thiazolidine was reacted with isobutyl bromide according to Method D2f to afford (4S)-2-(4-cyano-2-(trifluoromethyl)phenylimino)-3,4-diisobutyl-1,3-thiazolidine trifluoroacetate salt.

Quelle

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