Nitrogen → HCID 68506955, compound

HRID 39052Notes

Reaction equation

[CH2:1]([NH:5][C:6](=[O:49])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]([NH:19][S:20]([CH2:23][CH:24]=C)(=[O:22])=[O:21])=[O:18])[CH:15]=2)[C:10]([CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)=[C:9]1[C:32]1[CH:33]=[C:34]2[C:39](=[CH:40][CH:41]=1)[N:38]=[C:37]([C:42]1[S:46][C:45]([CH3:47])=[N:44][C:43]=1[CH3:48])[CH:36]=[CH:35]2)[CH2:2][CH:3]=C.N#N>ClCCCl.CC(C)OC1C(C=[Ru](Cl)([P](C2CCCCC2)(C2CCCCC2)C2CCCCC2)Cl)=CC=CC=1>[CH:26]1([C:10]2[C:11]3[CH:12]=[CH:13][C:14]4[C:17](=[O:18])[NH:19][S:20](=[O:22])(=[O:21])[CH2:23][CH:24]=[CH:3][CH2:2][CH2:1][NH:5][C:6](=[O:49])[CH2:7][N:8]([C:16]=3[CH:15]=4)[C:9]=2[C:32]2[CH:33]=[C:34]3[C:39](=[CH:40][CH:41]=2)[N:38]=[C:37]([C:42]2[S:46][C:45]([CH3:47])=[N:44][C:43]=2[CH3:48])[CH:36]=[CH:35]3)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of intermediate 17-5 (260 mg, 0.373 mmol) in DCE (400 mL) was bubbled through with N2 during 2 h. Hoveyda-Grubbs 1st generation catalyst (45 mg, 0.2 eq) was next added and the reaction mixture was heated at 80° C. under N2 overnight. The reaction mixture was then concentrated under reduced pressure and purified by flash chromatography (CH2Cl2/methanol 95:5) to give the desired product 18 as a gray powder after recrystallization from CH2Cl2/isopropyl ether; m/z=668 (M+H+), NMR (DMSO-d6): δ (ppm) 1.20-1.30 (m, 3H), 1.63-1.93 (m, 9H), 2.34 (m, 2H), 2.66 (m, 1H), 2.67 (s, 3H), 2.73 (s, 3H), 3.23 (m, 2H), 4.50 (s, 2H), 5.64 (m, 2H), 7.45 (m, 1H), 7.73-8.12 (m, 6H), 8.47 (broad s, 1H, NHCO), 8.54 (d, J=8.4 Hz, 1H), 11.47 (broad s, 1H, NHSO2).

Workup

concentrationThe reaction mixture was then concentrated under reduced pressure
custompurified by flash chromatography (CH2Cl2/methanol 95:5)

Sources & evidence

ORD record: ord-00af4674bb9c4e6aa0f722da9a0ce038
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08524716B2

Reaction notes

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