1,4-Dioxane hydrochloride → HCID 67250732, compound

HRID 2426786Notes

Reaction equation

O1CCOCC1.[ClH:7].[O:8]=[C:9]1[NH:13][C:12](=[O:14])[O:11][N:10]1[CH2:15][C:16]1[CH:49]=[CH:48][C:19]([O:20][CH2:21][C:22]2[C:23]([CH3:47])=[C:24]([C:28]3[CH:33]=[CH:32][C:31]([O:34][CH2:35][CH2:36][CH2:37][NH:38]C(=O)OC(C)(C)C)=[CH:30][C:29]=3[CH3:46])[CH:25]=[CH:26][CH:27]=2)=[CH:18][CH:17]=1>C(OCC)(=O)C>[ClH:7].[NH2:38][CH2:37][CH2:36][CH2:35][O:34][C:31]1[CH:32]=[CH:33][C:28]([C:24]2[CH:25]=[CH:26][CH:27]=[C:22]([CH2:21][O:20][C:19]3[CH:48]=[CH:49][C:16]([CH2:15][N:10]4[C:9](=[O:8])[NH:13][C:12](=[O:14])[O:11]4)=[CH:17][CH:18]=3)[C:23]=2[CH3:47])=[C:29]([CH3:46])[CH:30]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Under ice-cooling, a 4 M hydrogen chloride dioxane solution (15 ml) was added dropwise to a mixture of tert-butyl (3-{[3′-({4-[(3,5-dioxo-1,2,4-oxadiazolidin-2-yl)methyl]phenoxy}methyl)-2,2′-dimethylbiphenyl-4-yl]oxy}propyl)carbamate (1.95 g) and ethyl acetate (5 ml), followed by stirring at 0° C. for a while and then stirring at room temperature for 1.5 hours. The solvent was evaporated under a reduced pressure, and the solid precipitated was collected by filtration and dried by heating under a reduced pressure to obtain 2-(4-{[4′-(3-aminopropoxy)-2,2′-dimethylbiphenyl-3-yl]methoxy}benzyl)-1,2,4-oxadiazolidine-3,5-dione hydrochloride (1.53 g) as a white solid.

Workup

temperatureUnder ice-cooling
stirringstirring at room temperature for 1.5 hours
customThe solvent was evaporated under a reduced pressure
customthe solid precipitated
filtrationwas collected by filtration
customdried
temperatureby heating under a reduced pressure

Sources & evidence

ORD record: ord-22876a4231124cfb93d4171933307410
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07968552B2

Reaction notes

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