Potassium Carbonate → HCID 178523437, compound

HRID 2120274Notes

Reaction equation

[NH:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=2)=[N:2]1.C(=O)([O-])[O-].[K+].[K+].[CH2:19]([O:26][C:27]([NH:29][CH2:30][CH2:31]OS(C)(=O)=O)=[O:28])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CS(C)=O>[CH2:19]([O:26][C:27](=[O:28])[NH:29][CH2:30][CH2:31][O:12][C:9]1[CH:10]=[CH:11][C:6]([C:3]2[CH:4]=[CH:5][NH:1][N:2]=2)=[CH:7][CH:8]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A round-bottomed flask was charged with 4-pyrazol-3-yl-phenol (840 mg, 5.25 mmol), potassium carbonate (2.17 g, 15.7 mmol), and methanesulfonic acid 2-benzyloxycarbonylamino-ethyl ester (C. A. Townsend, et al., Tetrahedron, 47, 2591 (1991)) (2.86 g, 10.5 mmol) in 10.5 ml of dry dimethylsulfoxide. The resulting solution was heated to about 70° C. for about four days. The reaction mixture was then poured into 1 N HCL, and the aqueous phase was extracted twice with ethyl acetate. The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude material was purified by column chromatography (methylene chloride to 2% methanol/methylene chloride) to afford 1.09 g (61% yield) of desired product. LRMS ([M+H+])=338.1.

Workup

additionThe reaction mixture was then poured into 1 N HCL
extractionthe aqueous phase was extracted twice with ethyl acetate
washThe combined organic extracts were washed with brine
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude material was purified by column chromatography (methylene chloride to 2% methanol/methylene chloride)

Sources & evidence

ORD record: ord-9a3d6dbe70c547a7b61fc9ba7a50ccf5
Source dataset: uspto-grants-2004_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06689888B2

Reaction notes

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