2-(2-Methyl-4-nitrophenylimino)-3-isobutyl-4-methylene-1,3-thiazolidin-5-one → 2-(2-Methyl-4-nitrophenylimino)-3-isobutylspiro[1,3-thiazolidine-4,2'-bicyclo[2.2.1]heptane]

HRID 276279

Reaktionsgleichung

Reaktionsgleichung von HRID 276279
Cl.[CH2:2]([N:6]1[C@@H:10]([C:11](OC)=O)[CH2:9][S:8][C:7]1=[N:15][C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][C:17]=1[CH3:25])[CH:3]([CH3:5])[CH3:4].C(N1C(=C)C(=O)SC1=N[C:38]1[CH:43]=CC([N+]([O-])=O)=[CH:40][C:39]=1[CH3:47])C(C)C>CCOC(C)=O>[CH3:25][C:17]1[CH:18]=[C:19]([N+:22]([O-:24])=[O:23])[CH:20]=[CH:21][C:16]=1[N:15]=[C:7]1[N:6]([CH2:2][CH:3]([CH3:5])[CH3:4])[C:10]2([CH2:40][CH:39]3[CH2:47][CH:11]2[CH2:43][CH2:38]3)[CH2:9][S:8]1

Komponenten

4

Edukt 2

HCID 183160452-(2-Methyl-4-nitrophenylimino)-3-isobutyl-4-methylene-1,3-thiazolidin-5-oneHCID 69993936(S)-3-isobutyl-4-carbomethoxy-2-(2-methyl-4-nitrophenylimino)-1,3-thiazolidine HCl salt2×

Produkt 1

HCID 183161122-(2-Methyl-4-nitrophenylimino)-3-isobutylspiro[1,3-thiazolidine-4,2'-bicyclo[2.2.1]heptane]

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

(R)-N-Isobutylserine methyl ester HCl salt (Method B3a; 2.28 g, 10.8 mmol) was treated with SOCl2 followed by 2-methyl-4-nitrophenyl isothiocyanate in a manner analogous to Method C2a. The resulting material was purified by column chromatography (SiO2, gradient from hexane to 10% EtOAc/hex) to give 3-isobutyl-4-methylene-2-(2-methyl-4-nitrophenylimino)-1,3-thiazolidin-5-one (0.028 g, 10%) followed by (S)-3-isobutyl-4-carbomethoxy-2-(2-methyl-4-nitrophenylimino)-1,3-thiazolidine HCl salt (0.192 g, 56%). 3-Isobutyl-4-methylene-2-(2-methyl-4-nitrophenylimino)-1,3-thiazolidin-5-one: TLC (25% EtOAc/hex) Rf 0.40. (S)-3-isobutyl-4-carbomethoxy-2-(2-methyl-4-nitrophenylimino)-1,3-thiazolidine HCl salt: TLC (free base, 25% EtOAc/hex) Rf0.50.

Quellen und Nachweise

ORD-Eintrag
ord-d0f2f738c0a24882874d29e0b9cb4933
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06353006B1

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