Reaktion #363614

ord-fca18c3d6f2b45a09b90cc168c051360

Reaktionsgleichung

CC(C)C[C@H](N)CO
(1S)-1-(Hydroxymethyl)-3-methylbutylamine
NCCO
2-hydroxyethylamine
CC(C)CN[C@H](CO)CC(C)C
(2S)-4-methyl-2-(isobutylamino)pentanol
CC(C)C[NH3+].[Cl-]
N-(isobutyl)ammonium chloride
COC(=O)[C@@H](N)CC(C)C
(L)-leucine methyl ester
O=[N+]([O-])c1ccc(N=C=S)cc1
4-Nitrophenyl isothiocyanate
CC(C)C[NH3+].[Cl-]
N-(isobutyl)ammonium chloride
→
CC(C)CC1CN(CC(C)C)C(=Nc2ccc([N+](=O)[O-])cc2)S1
2-(4-nitrophenylimino)-3,5-diisobutyl-1,3-thiazolidine

Edukte

CC(C)C[C@H](N)CO
(1S)-1-(Hydroxymethyl)-3-methylbutylamine
—
alcohol
NCCO
2-hydroxyethylamine
CC(C)CN[C@H](CO)CC(C)C
(2S)-4-methyl-2-(isobutylamino)pentanol
CC(C)C[NH3+].[Cl-]
N-(isobutyl)ammonium chloride
COC(=O)[C@@H](N)CC(C)C
(L)-leucine methyl ester
O=[N+]([O-])c1ccc(N=C=S)cc1
4-Nitrophenyl isothiocyanate
CC(C)C[NH3+].[Cl-]
N-(isobutyl)ammonium chloride

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. The 2-hydroxyethylamine was converted to (2S)-4-methyl-2-(isobutylamino)pentanol as described in Method B4c, Steps 1-2. The alcohol was converted to N-(1S)-1-(chloromethyl)-3-methylbutyl)-N-(isobutyl)ammonium chloride as described in Method B7c. 4-Nitrophenyl isothiocyanate was reacted with N-(1S)-1-(chloromethyl)-3-methylbutyl)-N-(isobutyl)ammonium chloride according to Method C1f to give 2-(4-nitrophenylimino)-3,5-diisobutyl-1,3-thiazolidine.

Quelle

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