Potassium Carbonate → Ethyl 3-{3-[(tert-butoxycarbonyl)amino]azetidin-1-yl}benzoate

HRID 1425358Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:12][NH:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].I[C:14]1[CH:15]=[C:16]([CH:22]=[CH:23][CH:24]=1)[C:17]([O:19][CH2:20][CH3:21])=[O:18].N1CCC[C@H]1C(O)=O.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.C(OCC)(=O)C.[Cu]I>[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:10][N:11]([C:14]2[CH:15]=[C:16]([CH:22]=[CH:23][CH:24]=2)[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:12]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 120 °C

Procedure

A suspension of 3-tert-butoxycarbonylaminoazetidine (300 mg, 1.74 mmol), ethyl 3-iodobenzoate (721 mg, 2.61 mmol) and copper (I) iodide (66 mg, 0.35 mmol), proline (80 mg, 0.70 mmol) and potassium carbonate (721 mg, 5.22 mmol) in DMSO was stirred at 120° C. for two hours. The reaction solution was diluted with ethyl acetate and then filtered. The filtrate was washed with brine and then dried over anhydrous magnesium sulfate. Following filtration, the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=4/1) to obtain 319 mg of the title compound as a milk white solid (57%).

Workup

filtrationfiltered
washThe filtrate was washed with brine
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltration
customthe solvent was evaporated under reduced pressure
customThe resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=4/1)

Sources & evidence

ORD record: ord-86ce76e8ecee4b03989dd1b92f6039f8
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08927588B2

Reaction notes

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