Ethyl orthoformate → 4-[N-[1-[N-(benzofuran-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-[2-(tetrazol-1-yl)phenyl]piperidin-3-ol

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Reaction Steps

The mixture of 4-[N-[1-[N-(benzofuran-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-(2-aminophenyl)piperidin-3-one (2 g, 4 mmol) obtained in Step 2 of Example 43, sodium azide (NaN3; 409 mg, 6.2 mmol) and triethyl orthoformate (1.1 ml, 6.7 mmol) was refluxed in 10 ml of acetic acid for about 4 hours. The reaction mixture was cooled to room temperature. 10 ml of ice water was added to the reaction mixture, which was then stirred for about 48 hours. The resulting residue was filtered and dried to give 0.6 g of the titled compound.

Provenance & Evidence