Reaktionsgleichung
[CH2:1]([C:3]1[CH:8]=[C:7]([C:9]#[N:10])[CH:6]=[CH:5][C:4]=1[N:11]=[C:12]=[S:13])[CH3:2].[Cl-].[OH:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C@H:23]([NH2+:26][CH2:27][CH:28]([CH3:30])[CH3:29])[CH2:24][Cl:25])=[CH:18][CH:17]=1>>[ClH:25].[CH2:1]([C:3]1[CH:8]=[C:7]([C:9]#[N:10])[CH:6]=[CH:5][C:4]=1[N:11]=[C:12]1[N:26]([CH2:27][CH:28]([CH3:29])[CH3:30])[C@@H:23]([CH2:22][C:19]2[CH:18]=[CH:17][C:16]([OH:15])=[CH:21][CH:20]=2)[CH2:24][S:13]1)[CH3:2]Komponenten
Versuchsvorschrift
(1S)-1-(4-Hydroxyphenylmethyl)-2-hydroxyethylamine was made from (L)-tyrosine methyl ester as described in Method B1b. The 2-hydroxyethylamine was converted to (4S)-2-isopropyl-4-(4-hydroxyphenylmethyl)-1,3-oxazolidine according to Method B4c, Step 1. The oxazolidine was reduced to N-((1S)-1-(4-hydroxyphenylmethyl)-2-hydroxyethyl)-N-isobutylamine according to Method B4c, Step 2. The resulting 2-hydroxyethylamine was treated with SOCl2 according to Method B7c to give N-((1S)-1-(4-hydroxyphenylmethyl)-2-chloroethyl)-N-isobutylammonium chloride. 2-Ethyl-4-cyanophenyl isothiocyanate was reacted with N-((1S)-1-(4-hydroxyphenylmethyl)-2-chloroethyl)-N-isobutylammonium chloride according to Method C1b to give (4S)-2-(2-ethyl-4-cyanophenylimino)-4-(4-hydroxyphenylmethyl)-3-isobutyl-1,3-thiazolidine HCl salt.
Quellen und Nachweise
- ORD-Eintrag
- ord-392de3479cf7429b8192c2e846c12bc0
- Quelldatensatz
- uspto-grants-2002_03
- Patentnummer
- US06353006B1
Verknüpfte Notizen
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