Hydroxylamine → HCID 11641261, compound

Participants

Reaction Steps

Part H: To a solution of the carboxylic acid of Part G (460 mg, 1.1 mmol) in DMF (10 mL) was added N-hydroxbenzotriazole.H2O (180 mg, 1.33 mmol) and after 5 minutes of stirring was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (299 mg, 1.56 mmol). After 10 additional minutes 4-methylmorpholine (0.49 mL, 4.45 mmol) and 50% aqueous hydroxylamine (0.22 mL, 3.34 mmol) and the solution stirred for 24 hours. An additional aliquot of each reagent was added and the solution stirred for an additional 48 hours. The solution was diluted with H2O, extracted with chloroform, washed with satd. NaCl and dried over MgSO4. Reverse phase HPLC (acetonitrile/H2O) provided the hydroxamate compound as a white solid (N-hydroxy-4-[[(4-phenoxyphenyl)-sulfonyl]-methyl]-1-(2-propynyl)-4-piperidinecarboxamide, monohydrochloride; 200 mg, 42%). HRMS calc'd for C22H24N2O5S: 429.1489, found 429.1480. Anal. calc'd for C22H24N2O5S: C, 61.66; H, 5.64; N, 6.54; S, 7.48. Found: C, 61.33; H, 5.68; N, 6.36; S, 7.35.

Provenance & Evidence