Reaktion #363624

ord-aa1e1249c8834f7a81b27609e2a90363

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([N+](=O)[O-])ccc1N=C=S
2-Methyl-4-nitrophenyl isothiocyanate
NCCO
2-hydroxyethylamine
Cc1cc([N+](=O)[O-])ccc1N=C1N[C@@H](CC(C)C)CS1
(4S)-2-(2-methyl-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-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 1-chloro-3,3-dimethyl-2-butanone according to Method D2a to afford (4S)-2-(2-methyl-4-nitrophenylimino)4-isobutyl-3-(2-oxo-3,3-dimethyl-1-butyl)-1,3-thiazolidine.

Quelle

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