Potassium Carbonate → tert-butyl N-[2-(3-{5-[2-(methoxymethyl)-2'-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}phenyl)ethyl]-N-methylglycinate

HRID 2410595Notes

Reaction equation

CS(OC[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]2[N:18]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[CH3:31])=[C:21]([CH2:32][O:33][CH3:34])[CH:20]=3)[O:16][N:15]=2)[CH:9]=1)(=O)=O.[C:35](=O)([O-])[O-].[K+].[K+].Cl.[CH3:42][NH:43][CH2:44][C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46]>O1CCOCC1.C(Cl)Cl.O>[CH3:34][O:33][CH2:32][C:21]1[CH:20]=[C:19]([C:17]2[O:16][N:15]=[C:14]([C:10]3[CH:9]=[C:8]([CH2:7][CH2:42][N:43]([CH3:35])[CH2:44][C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[CH:13]=[CH:12][CH:11]=3)[N:18]=2)[CH:24]=[CH:23][C:22]=1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH3:31]

Participants

Conditions

Temperature: 130 °C

Procedure

To a solution of 2-(3-{5-[2-(methoxymethyl)-2′-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}phenethyl methanesulfonate (0.2 mmol) in dioxane (2 mL) was added potassium carbonate (165 mg, 1.2 mmol) and tert-butyl N-methylglycinate, hydrochloride salt (0.60 mmol). The mixture was heated at 130° C. for 72 hours, diluted with DCM (5 mL) and water (5 mL). The aqueous layer was extracted with DCM (3×20 mL), the combined organic fractions were dried (MgSO4), filtered and the solvent removed in vacuo. The residue was purified by flash chromatography (silica, Pet Ether/EtOAc) to give the title compound as a colorless oil (86 mg, 72%).

Workup

extractionThe aqueous layer was extracted with DCM (3×20 mL)
dry with materialthe combined organic fractions were dried (MgSO4)
filtrationfiltered
customthe solvent removed in vacuo
customThe residue was purified by flash chromatography (silica, Pet Ether/EtOAc)

Sources & evidence

ORD record: ord-0eae7a0b999b4956bef74643506446e2
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815919B2

Reaction notes

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