Acetic Acid → HCID 69132047, compound

Participants

Reaction Steps

A mixture of 400 mg of the above amide, 298 mg KCN, 1.59 g MnO2 and 157 microL acetic acid was suspended in 16 mL MeOH and the reaction was capped and stirred 2 days. The reaction mixture was filtered through diatomaceous earth, concentrated, and flash-chromatographed eluting with 5% MeOH/CH2Cl2 to provide 254 mg (60%) 3-amino-6-[4-(tert-butyl-dimethyl-silanyloxy)-piperidin-1-yl]-2-carbamoyl-thieno[2,3-b]pyridine-4-carboxylic acid methyl ester as determined by NMR(DMDO). Further elution with 25% MeOH/CH2Cl2/1% HOAc brought down 151 mg (36%) of the corresponding carboxylic acid as determined by NMR(DMDO).

Provenance & Evidence