Reaktion #363660

ord-57d7b3c2bb2c4e53b0f574f60b8ff6f1

Reaktionsgleichung

CC(C)[C@H](N)CO
(1S)-1-Isopropyl-2-hydroxyethylamine
CC(C)[C@H]([NH3+])CCl.[Cl-]
(1S)-2-chloro-1-isopropylethylammonium chloride
Cc1cc([N+](=O)[O-])ccc1N=C=S
2-Methyl-4-nitrophenyl isothiocyanate
CC(C)[C@H]([NH3+])CCl.[Cl-]
(1S)-2-chloro-1-isopropylethylammonium chloride
→
Cc1cc([N+](=O)[O-])ccc1N=C1N[C@@H](C(C)C)CS1
(45)-2-(2-methyl-4-nitrophenylimino)-4-isopropyl-1,3-thiazolidine

Edukte

CC(C)[C@H](N)CO
(1S)-1-Isopropyl-2-hydroxyethylamine
CC(C)[C@H]([NH3+])CCl.[Cl-]
(1S)-2-chloro-1-isopropylethylammonium chloride
Cc1cc([N+](=O)[O-])ccc1N=C=S
2-Methyl-4-nitrophenyl isothiocyanate
CC(C)[C@H]([NH3+])CCl.[Cl-]
(1S)-2-chloro-1-isopropylethylammonium chloride

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

(1S)-1-Isopropyl-2-hydroxyethylamine was converted to (1S)-2-chloro-1-isopropylethylammonium chloride according to Method B7a. 2-Methyl-4-nitrophenyl isothiocyanate was reacted with (1S)-2-chloro-1-isopropylethylammonium chloride according to Method C1a to give (45)-2-(2-methyl-4-nitrophenylimino)-4-isopropyl-1,3-thiazolidine. The thiazolidine was reacted with isobutyl bromide according to Method D2a to afford (4S)-2-(2-methyl -4-nitrophenylimino)-4-isopropyl-3-isobutyl-1,3-thiazolidine HCl salt.

Quelle

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