Homoserine lactone hydrobromide → 4-(4-{4-[(benzyl{2-methyl-3-[(methylsulfonyl)amino]phenyl}amino)methyl]phenoxy}phenyl)-N-(2-oxotetrahydrofuran-3-yl)butanamide

HRID 1370929

Reaktionsgleichung

Reaktionsgleichung von HRID 1370929
[CH2:1]([N:8]([CH2:21][C:22]1[CH:40]=[CH:39][C:25]([O:26][C:27]2[CH:32]=[CH:31][C:30]([CH2:33][CH2:34][CH2:35][C:36](O)=[O:37])=[CH:29][CH:28]=2)=[CH:24][CH:23]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])[C:10]=1[CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br.[NH2:42][CH:43]1[CH2:48][CH2:47][O:46][C:44]1=[O:45]>>[CH2:1]([N:8]([CH2:21][C:22]1[CH:23]=[CH:24][C:25]([O:26][C:27]2[CH:28]=[CH:29][C:30]([CH2:33][CH2:34][CH2:35][C:36]([NH:42][CH:43]3[CH2:48][CH2:47][O:46][C:44]3=[O:45])=[O:37])=[CH:31][CH:32]=2)=[CH:39][CH:40]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH:15][S:16]([CH3:19])(=[O:17])=[O:18])[C:10]=1[CH3:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

3

Edukt 2

HCID 73508Homoserine lactone hydrobromideHCID 185122134-(4-{4-[(benzyl{2-methyl-3-[(methylsulfonyl)amino]phenyl}amino)methyl]phenoxy}phenyl)butanoic Acid

Produkt 1

HCID 102331344-(4-{4-[(benzyl{2-methyl-3-[(methylsulfonyl)amino]phenyl}amino)methyl]phenoxy}phenyl)-N-(2-oxotetrahydrofuran-3-yl)butanamide

Versuchsvorschrift

The product from Example 100 (56 mg, 0.1 mmole) and α-Amino-γ-butyrolactone hydrobromide (36 mg, 0.2 mmole) were processed as in Examples 213A and 224B to provide the title compound. 1H NMR (500 MHz, DMSO-d6) δ8.95 (s, 1 H), 8.31 (d, 1 H), 7.26 (m, 6 H), 7.18 (m, 3 H), 7.04 (m, 1 H), 6.97 (m, 2 H), 6.88 (m, 4 H), 4.53 (dd, 1 H), 4.34 (t, 1 H), 4.20 (m, 1 H), 4.06 (s, 2 H), 4.02 (s, 2 H), 3.17 (s, 3 H), 2.91 (s, 3 H), 2.55 (t, 2 H), 2.39 (m, 2 H), 2.13 (t, 2 H), 1.67-1.90 (m, 2 H); MS (APCI+) m/z 642 (M+H)+.

Quellen und Nachweise

ORD-Eintrag
ord-2c612447f9634097bf5639b3b8c5e515
Quelldatensatz
uspto-grants-2003_06
Patentnummer
US06583180B2

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