Reaktion #363652

ord-95adf840d7bd42c58444000ce7f94ab8

Reaktionsgleichung

O=[N+]([O-])c1ccc(N=C=S)c2ccccc12
4-nitro-1-naphthyl isothiocyanate
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)c2ccccc12
4-Nitro-1-naphthyl isothiocyanate
CC(C)C[C@H](N)CO
(1S)-1-(hydroxymethyl)-3-methylbutylamine
Nc1ccc([N+](=O)[O-])c2ccccc12
4-Nitro-1-naphthylamine
→
CC(C)C[C@H]1CSC(=Nc2ccc([N+](=O)[O-])c3ccccc23)N1
(4S)-2-(4-nitro-1-naphthylimino)-4-isobutyl-1,3-thiazolidine

Edukte

O=[N+]([O-])c1ccc(N=C=S)c2ccccc12
4-nitro-1-naphthyl isothiocyanate
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)c2ccccc12
4-Nitro-1-naphthyl isothiocyanate
CC(C)C[C@H](N)CO
(1S)-1-(hydroxymethyl)-3-methylbutylamine
Nc1ccc([N+](=O)[O-])c2ccccc12
4-Nitro-1-naphthylamine

Reagenzien

Keine

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. 4-Nitro-1-naphthylamine was converted to 4-nitro-1-naphthyl isothiocyanate according to Method A2b. 4-Nitro-1-naphthyl isothiocyanate was reacted with (1S)-1-(hydroxymethyl)-3-methylbutylamine to Method C2a to give (4S)-2-(4-nitro-1-naphthylimino)-4-isobutyl-1,3-thiazolidine. The thiazolidine was reacted with isobutyl bromide according to Method D2a to give (4S)-2-(4-nitro-1-naphthylimino)-3,4-diisobutyl-1,3-thiazolidine.

Quelle

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