Hydrochloric Acid → HCID 19366862, compound

Participants

Reaction Steps

Part C: (471 mg, 1.8 mmol) of triphenylphosphine and (520 mg, 1.8 mmol) of N-[1-(hydroxymethyl)-2-[(4-methoxyphenyl)sulfonyl)ethyl)acetamide were dissolved in 15 mL of tetrahydrofuran and cooled to zero C. under nitrogen atmosphere. To this was added (313 mg, 1.8 mmol) of diethyldiazodicarboxylate, followed by (140 mg, 1.8 mmol) of thioacetic acid and the solution stirred for 2 hours. The resulting clear solution was concentrated by rotory evaporation and subjected to silica gel chromatography using 15% methanol in ethyl acetate as the eluant to provide a mixture of triphenylphosphine oxide and the desired N-[1-(thioacetylmethyl)-2-[(4-methoxyphenyl)sulfonyl)ethyl)acetamide in equal molar ratios. This mixture was dissolved in 10 ml of methanol and to this was added 1 mL of 25% sodium methoxide in methanol and this stirred for 30 minutes. The solution was acidified with 1N hydrochloric acid and extracted with ethyl acetate. The resulting organics were concentrated and purified by reverse phase C18 chromatography to yield 150 mg of N-[1-(mercaptomethyl)-2-[(4-methoxyphenyl)sulfonyl)ethyl)acetamide, m/e=310 (M+Li).

Provenance & Evidence