Ethanolamine → (4S)-2-(2-methyl-4-nitrophenylimino)-3,4-diisobutyl-1,3-thiazolidine

HRID 276469

Reaktionsgleichung

Reaktionsgleichung von HRID 276469
OC[C@@H](N)CC(C)C.COC(=O)[C@H](CC(C)C)N.OCCN.[CH3:23][CH:24]([CH3:34])[CH2:25][C@H:26]([NH:29][CH2:30][CH:31]([CH3:33])[CH3:32])[CH2:27]O.[Cl-].C([NH3+])C(C)C.[CH3:41][C:42]1[CH:47]=[C:46]([N+:48]([O-:50])=[O:49])[CH:45]=[CH:44][C:43]=1[N:51]=[C:52]=[S:53]>>[CH3:41][C:42]1[CH:47]=[C:46]([N+:48]([O-:50])=[O:49])[CH:45]=[CH:44][C:43]=1[N:51]=[C:52]1[N:29]([CH2:30][CH:31]([CH3:33])[CH3:32])[C@@H:26]([CH2:25][CH:24]([CH3:34])[CH3:23])[CH2:27][S:53]1

Komponenten

7

Edukt 6

HCID 700Ethanolamine2×HCID 21133Isobutylaminehydrochloride2×HCID 65105(+)-L-Leucine methyl esterHCID 111307L-LeucinolHCID 1456212-Methyl-4-nitrophenyl isothiocyanateHCID 22951222(2S)-4-methyl-2-(isobutylamino)pentanol

Produkt 1

HCID 10291492(4S)-2-(2-methyl-4-nitrophenylimino)-3,4-diisobutyl-1,3-thiazolidine

Versuchsvorschrift

(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.

Quellen und Nachweise

ORD-Eintrag
ord-70e26867b02c4090acfc1fa3aedbbcdd
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06353006B1

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