Reaktion #363634

ord-e73282e7c7654b7eb7f9c60f840c9481

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
O=[N+]([O-])c1ccc(N=C=S)c(C(F)(F)F)c1
2-(Trifluoromethyl)4-nitrophenyl isothiocyanate
NCCO
2-hydroxyethylamine
CC(C)C[C@H]1CSC(=Nc2ccc([N+](=O)[O-])cc2C(F)(F)F)N1
(4S)-2-(2-(trifluoromethyl)-4-nitrophenylimino)-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-(Trifluoromethyl)4-nitrophenyl isothiocyanate was reacted with (1S)-1-(chloromethyl)-3-methylbutanammonium chloride according to Method C1c to give (4S)-2-(2-(trifluoromethyl)-4-nitrophenylimino)-4-isobutyl-1,3-thiazolidine. The thiazolidine was reacted with isobutyl bromide according to Method D2f to afford (4S)-2-(2-(trifluoromethyl)-4-nitrophenylimino)-3,4-diisobutyl-1,3-thiazolidine trifluoroacetate salt.

Quelle

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