L-(+)-Cysteine → (2R)-2-amino-3-{[2-(5-methyl-4-oxo-5-phenyl-4,5-dihydrofuran-2-yl)-1-thien-3-ylethyl]thio}propanoic acid

HRID 50030

Reaktionsgleichung

Reaktionsgleichung von HRID 50030
[CH3:1][C:2]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:6](=[O:7])[CH:5]=[C:4](/[CH:8]=[CH:9]/[C:10]2[CH:14]=[CH:13][S:12][CH:11]=2)[O:3]1.[NH2:21][C@H:22]([C:25]([OH:27])=[O:26])[CH2:23][SH:24]>>[NH2:21][C@@H:22]([CH2:23][S:24][CH:9]([C:10]1[CH:14]=[CH:13][S:12][CH:11]=1)[CH2:8][C:4]1[O:3][C:2]([CH3:1])([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:6](=[O:7])[CH:5]=1)[C:25]([OH:27])=[O:26]

Komponenten

3

Edukt 2

HCID 5862L-(+)-CysteineHCID 11300541(E)-2-methyl-2-phenyl-5-[2-(3-thienyl)ethenyl]-3(2H)-furanone

Produkt 1

HCID 10179320(2R)-2-amino-3-{[2-(5-methyl-4-oxo-5-phenyl-4,5-dihydrofuran-2-yl)-1-thien-3-ylethyl]thio}propanoic acid

Versuchsvorschrift

Following the procedure of Method C, Example 1, (E)-2-methyl-2-phenyl-5-[2-(3-thienyl)ethenyl]-3(2H)-furanone was reacted with L-cysteine to provide (2R)-2-amino-3-{[2-(5-methyl-4-oxo-5-phenyl-4,5-dihydrofuran-2yl)-1-thien-3-ylethyl]thio}propanoic acid: 1H NMR (DMSO-d6) δ1.50-1.60 (overlapping singlets, 3H), 2.70-3.10 (m, ˜2H), 4.00-4.25 (m, 1H), 4.64 (m, 1H), 5.50-5.57 (overlapping singlets, 1H), 7.12-7.38 (m, 6H), 7.52-7.63 (m, 2H), 8.35 (br s, ˜2H); MS (LR-ESI) m/z 402 (M-H calcd. for C20H20NO4S2 402)

Quellen und Nachweise

ORD-Eintrag
ord-d790d9abdbae4f89bc5f814f6b774d13
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06710078B2

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