Gamma-Aminobutyric Acid → 4-{4-[(4-Fluoro-2-methylsulfanyl-benzyl)-methyl-carbamoyl]-3-hydroxy-2-oxo-2,5-dihydro-pyrrol-1-yl}-butyric acid

HRID 2214671

Reaktionsgleichung

Reaktionsgleichung von HRID 2214671
CC1(C)[O:6][C:5](=[CH:7][C:8]([N:10]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=2[S:20][CH3:21])[CH3:11])=[O:9])[C:4](=[O:22])O1.[CH2:24]=O.[NH2:26][CH2:27][CH2:28][CH2:29][C:30]([OH:32])=[O:31]>>[F:19][C:16]1[CH:17]=[CH:18][C:13]([CH2:12][N:10]([CH3:11])[C:8]([C:7]2[CH2:24][N:26]([CH2:27][CH2:28][CH2:29][C:30]([OH:32])=[O:31])[C:4](=[O:22])[C:5]=2[OH:6])=[O:9])=[C:14]([S:20][CH3:21])[CH:15]=1

Komponenten

4

Edukt 3

HCID 119Gamma-Aminobutyric AcidHCID 712FormaldehydeHCID 696563232-(2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-(4-fluoro-2-methylsulfanyl-benzyl)-N-methyl-acetamide

Produkt 1

HCID 546917894-{4-[(4-Fluoro-2-methylsulfanyl-benzyl)-methyl-carbamoyl]-3-hydroxy-2-oxo-2,5-dihydro-pyrrol-1-yl}-butyric acidAusbeute 49 %

Versuchsvorschrift

2-(2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-(4-fluoro-2-methylsulfanyl-benzyl)-N-methyl-acetamide was reacted with paraformaldehyde and 4-amino-butyric acid as described in Method 44B to give the title compound as a white solid (0.05 g, 49% yield). 1HNMR (300 MHz, CDCl3) δ: 7.11 (1H, dd, J=8.42, 5.85 Hz), 6.91 (1H, dd, J=9.52, 2.57 Hz), 6.82 (1H, td, J=8.41, 2.56 Hz), 4.64 (2H, s), 4.15 (2H, s), 3.55 (2H, t, J=6.96 Hz), 2.98 (3H, s), 2.47 (3H, s), 2.38 (2H, t, J=6.95 Hz), 1.96–1.88 (2H, m).

Quellen und Nachweise

ORD-Eintrag
ord-248297ce0bd0447782822b0cea0cef41
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07109186B2

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