Ethanolamine → HCID 178428753, Verbindung

HRID 276448

Reaktionsgleichung

Reaktionsgleichung von HRID 276448
O[CH2:2][C@@H:3]([NH2:8])[CH2:4][CH:5]([CH3:7])[CH3:6].COC(=O)[C@H](CC(C)C)N.OCCN.[CH3:23][C:24]1[CH:29]=[C:28]([N+:30]([O-:32])=[O:31])[CH:27]=[CH:26][C:25]=1[N:33]=[C:34]=[S:35]>>[CH3:23][C:24]1[CH:29]=[C:28]([N+:30]([O-:32])=[O:31])[CH:27]=[CH:26][C:25]=1[N:33]=[C:34]1[NH:8][C@@H:3]([CH2:4][CH:5]([CH3:7])[CH3:6])[CH2:2][S:35]1

Komponenten

5

Edukt 4

HCID 700EthanolamineHCID 65105(+)-L-Leucine methyl esterHCID 111307L-LeucinolHCID 1456212-Methyl-4-nitrophenyl isothiocyanate

Produkt 1

HCID 178428753HCID 178428753, Verbindung

Versuchsvorschrift

(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 2-chloro-3,3-dimethyl-2-butanone according to Method D2a to give (4S)-2-(2-methyl-4-nitrophenylimino)-4-isobutyl-3-(2-oxo-3,3-dimethyl-1-butyl)-1,3-thiazolidine. The ketone was reduced according to Method D5a to afford (4S)-2-(2-methyl-4-nitrophenylimino)-4-isobutyl-3-(3,3-dimethyl-2-hydroxy-1-butyl)-1,3-thiazolidine.

Quellen und Nachweise

ORD-Eintrag
ord-d59834b6418d4928992c1b46e38f1d35
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06353006B1

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