Nitrogen → HCID 19366833, compound

Participants

Reaction Steps

Part A: To a stirred degassed (N2) solution of (20 g, 139 mmol) of N-acetyl-dehydroalanine methyl ester in 400 mL of methanol was added (19.5 g, 139 mmol) of 4-methoxythiophenol followed by 14.0 g, 140 mmol) of triethylamine and the resulting solution stirred for 2 hours. The resulting N-acetyl-β-(4-methoxythio-phenyl)-D,L-alanine methyl ester was oxidized in situ by the addition of 800 mL of methanol, 160 mL of water followed by (250 g, 417 mmol) of OXONE®. The suspension was stirred for 3 hours and then filtered through a fritted glass buchner funnel. The filtrate was concentrated by rotary evaporation and the concentrated material was partitioned between ethyl acetate and sodium bicarbonate. The organic layer was washed with brine, dried over magnesium sulfate, filtered and concentrated to a white solid which was triturated with cold ethyl acetate and filtered to yield 28.5 g of N-acetyl-β-(4-methoxyphenylsulfonyl)-D,L-alanine methyl ester.

Provenance & Evidence