Hydrogen Peroxide → (3aR,5S,6aR)-5-methyl-1-(4'-(6-oxopyridazin-1(6H)-yl)biphenyl-4-yl)octahydropyrrolo[3,4-b]pyrrole 5-oxide

HRID 912491

反応式

[CH3:1][N:2]1[CH2:9][C@@H:8]2[C@@H:4]([N:5]([C:10]3[CH:15]=[CH:14][C:13]([C:16]4[CH:21]=[CH:20][C:19]([N:22]5[C:27](=[O:28])[CH:26]=[CH:25][CH:24]=[N:23]5)=[CH:18][CH:17]=4)=[CH:12][CH:11]=3)[CH2:6][CH2:7]2)[CH2:3]1.[OH:29]O>C(Cl)Cl.CO>[CH3:1][N@+:2]1([O-:29])[CH2:9][C@@H:8]2[C@@H:4]([N:5]([C:10]3[CH:15]=[CH:14][C:13]([C:16]4[CH:21]=[CH:20][C:19]([N:22]5[C:27](=[O:28])[CH:26]=[CH:25][CH:24]=[N:23]5)=[CH:18][CH:17]=4)=[CH:12][CH:11]=3)[CH2:6][CH2:7]2)[CH2:3]1

参加物

反応条件

温度: 50 °C

実験手順

A solution of the product from Example 1G (5 g, 13.44 mmol) in DCM (80 mL) and MeOH (40 mL) was treated with hydrogen peroxide (5.2 mL, 30% in H2O, 53.8 mmol). The mixture was heated to 50° C. for 48 hours. The mixture was concentrated under reduced pressure to a smaller volume while still in a solution. The solution was loaded onto an ANALOGIX SuperFlash silica gel column (ANALOGIX is a registered trademark of Analogix Inc. of Burlington, Wis.) and eluted with NH4OH /MeOH/DCM (1/10/90) to obtain the slower moving component (comparing with Example 1H) as the title product. 1H NMR (300 MHz, DMSO) δ ppm 8.07 (m, 1 H), 7.70 (d, J=9 Hz, 2 H), 7.57 (d, J=9 Hz, 4 H), 7.50 (d, J=6 Hz, 1 H), 7.08 (dd, dd, J=9, 4.0 Hz, 1 H), 6.65 (d, J=9 Hz, 2 H), 4.48-4.54 (m, 1 H), 3.81-3.87 (m, 1 H), 3.66-3.74 (m, 2 H), 3.36-3.42 (m, 2 H), 3.24 (m, 1 H), 3.09 (s, 3 H), 2.11-2.17 (m, 1 H); MS (DCI,) M+=388.

後処理

concentrationThe mixture was concentrated under reduced pressure to a smaller volume while still in a solution
wash) and eluted with NH4OH /MeOH/DCM (1/10/90)
customto obtain the

出典と根拠

ORDレコード: ord-c4869d68476148a3874fd2544674298a
出典データセット: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US08026240B2

反応式

参加物

反応物 2

生成物 1

試薬・触媒・溶媒 2

反応条件

実験手順

後処理

出典と根拠

関連ノート