Reaktion #363651

ord-70e26867b02c4090acfc1fa3aedbbcdd

Reaktionsgleichung

CC(C)C[C@H](N)CO
(1S)-1-(Hydroxymethyl)-3-methylbutylamine
NCCO
2-hydroxyethylamine
NCCO
2-hydroxyethylamine
CC(C)CN[C@H](CO)CC(C)C
(2S)-4-methyl-2-(isobutylamino)pentan-1-ol
CC(C)C[NH3+].[Cl-]
N-(isobutyl)ammonium chloride
COC(=O)[C@@H](N)CC(C)C
(L)-leucine methyl ester
Cc1cc([N+](=O)[O-])ccc1N=C=S
2-Methyl-4-nitrophenyl isothiocyanate
CC(C)C[NH3+].[Cl-]
N-(isobutyl)ammonium chloride
→
Cc1cc([N+](=O)[O-])ccc1N=C1SC[C@H](CC(C)C)N1CC(C)C
(4S)-2-(2-methyl-4-nitrophenylimino)-3,4-diisobutyl-1,3-thiazolidine

Edukte

CC(C)C[C@H](N)CO
(1S)-1-(Hydroxymethyl)-3-methylbutylamine
NCCO
2-hydroxyethylamine
NCCO
2-hydroxyethylamine
CC(C)CN[C@H](CO)CC(C)C
(2S)-4-methyl-2-(isobutylamino)pentan-1-ol
CC(C)C[NH3+].[Cl-]
N-(isobutyl)ammonium chloride
COC(=O)[C@@H](N)CC(C)C
(L)-leucine methyl ester
Cc1cc([N+](=O)[O-])ccc1N=C=S
2-Methyl-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)pentan-1-ol as described in Method B4c. The resulting 2-hydroxyethylamine was converted to N-(1S)-1-(chloromethyl)-3-methylbutyl)-N-(isobutyl)ammonium chloride according to Method B7c. 2-Methyl-4-nitrophenyl isothiocyanate was reacted with N-(1S)-1-(chloromethyl)-3-methylbutyl)-N-(isobutyl)ammonium chloride to Method C1b to afford (4S)-2-(2-methyl-4-nitrophenylimino)-3,4-diisobutyl-1,3-thiazolidine.

Quelle

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