Methanol → HCID 67248086, compound

HRID 1027578Notes

Reaction equation

C(N(CC)CC)C.[OH:8][N:9]1[C:13](=[O:14])[C:12]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:11]2[C:10]1=[O:19].Br[CH2:21][CH:22]1[CH2:24][N:23]1[S:25]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[N+:34]([O-:36])=[O:35])(=[O:27])=[O:26].[CH3:37][OH:38]>O1CCOCC1>[CH3:37][O:38][C:10](=[O:19])[C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1[C:13]([N:9]1[CH2:24][CH:22]([NH:23][S:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[N+:34]([O-:36])=[O:35])(=[O:27])=[O:26])[CH2:21][O:8]1)=[O:14]

Participants

Conditions

Temperature: 50 °C

Procedure

Triethylamine (0.11 ml, 0.1 equiv) was added to a mixture of N-hydroxyphthalimide (1.13 g, 6.9 mmol) and 2-Bromomethyl-1-(2-nitro-benzenesulfonyl)-aziridine (7.6 mmol, 1.1 equiv) (prepared according to Org. Biomol. Chem. 2008, 6, 1902-1904) in anhydrous dioxane (4.5 ml). The reaction mixture was then heated to 50° C. over the weekend. Then methanol (2.5 ml) and triethylamine (1.1 ml, 1 equiv) were added and the reaction mixture was heated at 50° C. for another 4 hours. Volatiles were then removed in vacuo. Flash chromatography eluting with cyclohexane/ethyl actetate (1/1 then 3/7) afforded 2.46 g of the title compound (5.67 mmol, 74%). LCMS (Method E) 1.55 min, M+H 435. 1H-NMR (CDCl3, 400 MHz): 8.21-8.11 (m, 1H), 8.00 (d, 1H), 7.90-7.67 (m, 3H), 7.63-7.56 (m, 1H), 7.55-7.46 (m, 1H), 7.41 (d, 1H), 6.87-6.73 (m, 1H), 4.77-4.67 (m, 1H), 4.22-3.95 (m, 5H), 3.93-3.75 (m, 2H).

Workup

temperaturethe reaction mixture was heated at 50° C. for another 4 hours
customVolatiles were then removed in vacuo
washFlash chromatography eluting with cyclohexane/ethyl actetate (1/1

Sources & evidence

ORD record: ord-f9766d95967f4f0da46a5dc4ee8f4868
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735362B2

Reaction notes

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