(1S,2R)-(+)-Norephedrine → 2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-chloro-n-((2s, 1r)-2-hydroxy-1-methyl-2-phenyl-ethyl)-benzamide

HRID 1593858

Reaktionsgleichung

Reaktionsgleichung von HRID 1593858
[N:1]1[S:5][N:4]=[C:3]2[C:6]([S:10]([NH:13][C:14]3[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:15]=3[C:16]([OH:18])=O)(=[O:12])=[O:11])=[CH:7][CH:8]=[CH:9][C:2]=12.[CH3:24][CH:25]([NH2:34])[CH:26]([OH:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>>[N:1]1[S:5][N:4]=[C:3]2[C:6]([S:10]([NH:13][C:14]3[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:15]=3[C:16]([NH:34][C@H:25]([CH3:24])[C@@H:26]([OH:33])[C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)=[O:18])(=[O:12])=[O:11])=[CH:7][CH:8]=[CH:9][C:2]=12

Komponenten

3

Edukt 2

HCID 4786(1S,2R)-(+)-NorephedrineHCID 160906632-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-chlorobenzoic acid

Produkt 1

HCID 115189982-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-chloro-n-((2s, 1r)-2-hydroxy-1-methyl-2-phenyl-ethyl)-benzamide

Versuchsvorschrift

2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-chlorobenzoic acid was coupled with (1S,2R)-(+)-norephedrine as in EXAMPLE 1, Part C. HPLC: RT=10.13 min. MS (ESI−): mass calcd. for C22H19ClN4O4S2, 502.05; m/z found, 501 [M−H]−. 1H NMR (400 MHz, CDCl3): 11.69 (s, 1H), 8.37 (dd, J=7.0, 1.0, 1H), 8.22 (dd, J=8.8, 1.0, 1H), 7.73 (d, J=2.0, 1H), 7.72 (dd, J=8.8, 7.0, 1H), 7.41-7.29 (m, 5H), 7.24 (d, J=8.4, 1H), 6.93 (dd, J=8.4, 2.0, 1H), 6.28 (br d, J=8.3, 1H), 4.98 (d, J=3.0, 1H), 4.45 (ddq, J=8.3, 6.9, 3.0, 1H), 2.60 (br s, 1H), 1.05 (d, J=6.9, 3H).

Quellen und Nachweise

ORD-Eintrag
ord-48e278b9d7f0404691ef94b37a191045
Quelldatensatz
uspto-grants-2007_11
Patentnummer
US07297816B2

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